5-Bromo-1,3-dichloro-2-fluorobenzene

light yellow liquid

A dry, argon-flushed Schienk-flask equipped with a magnetic stirrer and a septum was charged with 20 mL freshly titrated iPrMgClLiCI (1.24 M in THE, 1.0 equiv.) to which 3.8 mL of diisopropylamine (1.1 equiv.) was added dropwise at 25 00. The reaction mixture was stirred at this temperature until gasevolution was completed (ca. 48 h). The formed precipitate was dissolved with additional dry THE. The fresh solution of iPr2NMgCILiCI in THE was titrated at 25 00 with benzoic acid and 4- (phenylazo)diphenylamine as an indicator. A concentration of 0.59 M was obtained.To a solution of 4-bromo-2-chloro-1 -fluoro-benzene (0.209 g, 1 .00 mmol) in THE (1 mL) was added iPr2NMgCILiCI (0.59 M, 3.39 ml, 2.00 mmol) at 25 00 and the resulting mixture was stirred for 15 mm at25 c Hexachloro-2-propanone (0.397 g, 1 .50 mmol) was added at 0 00 and the mixture was stirred for15 mm. The resulting mixture was then quenched with sat. aq. NH4CI, extracted with ethyl acetate and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo. Quantitative GO measurement showed that the ratio between 5-bromo-1 , 3-dichloro-2-fluoro-benzene and regioisomer is about 12:1. Purification by flash column chromatography (Si02, i-hexane) furnished 5-bromo-1 , 3-dichloro-2-fluoro-benzene (0.190 g) as a colorless oil.1-(3, 5-dichloro-4-fluorophenyl)-2, 2, 2-trifluoroethan-1-one (Intermediate Compound 9) (0328) (0329) 9 (0330) [0164] To a cooled (10 C) solution of A stirred mixture of Example 48 Preparation of (E)-1, 3-dichloro-2-fluoro-5-(4-methoxystyryl)benzene (C67) A stirred mixture of A dry, argon-flushed Schienk-flask equipped with a magnetic stirrer and a septum was charged with 20 mL freshly titrated iPrMgClLiCI (1.24 M in THE, 1.0 equiv.) to which 3.8 mL of diisopropylamine (1.1 equiv.) was added dropwise at 25 00. The reaction mixture was stirred at this temperature until gasevolution was completed (ca. 48 h). The formed precipitate was dissolved with additional dry THE. The fresh solution of iPr2NMgCILiCI in THE was titrated at 25 00 with benzoic acid and 4- (phenylazo)diphenylamine as an indicator. A concentration of 0.59 M was obtained.To a solution of 4-bromo-2-chloro-1 -fluoro-benzene (0.209 g, 1 .00 mmol) in THE (1 mL) was added iPr2NMgCILiCI (0.59 M, 3.39 ml, 2.00 mmol) at 25 00 and the resulting mixture was stirred for 15 mm at25 c Hexachloro-2-propanone (0.397 g, 1 .50 mmol) was added at 0 00 and the mixture was stirred for15 mm. The resulting mixture was then quenched with sat. aq. NH4CI, extracted with ethyl acetate and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo. Quantitative GO measurement showed that the ratio between 5-bromo-1 , 3-dichloro-2-fluoro-benzene and regioisomer is about 12:1. Purification by flash column chromatography (Si02, i-hexane) furnished 5-bromo-1 , 3-dichloro-2-fluoro-benzene (0.190 g) as a colorless oil.

Molecular Weight:243.88
XLogP3:4
Hydrogen Bond Acceptor Count:1
Exact Mass:241.87010
Monoisotopic Mass:241.87010
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes