2-Chloro-4-methylbenzaldehyde

165 ml (413 mmol) of 2.5 M nBuLi in hexanes was added dropwise over 1 h to a solution of 82.2 g (400 mmol) of 4-bromo-3-chlorotoluene in 400 ml of THF cooled to -88 °C. The resulting mixture was stirred for 30 min at this temperature, and then 44.0 g (602 mmol) of DMF was added dropwise by vigorous stirring for 10 min. The reaction mixture was stirred overnight at room temperature, and then 100 ml of water and 400 ml of 3 N HC1 were added at 0 °C. The organic layer was separated, the aqueous layer was extracted with 2 x 125 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then passed through a short layer of silica gel 60 (40-63 μιη). The silica gel layer was additionally washed by 50 ml of dichloromethane. The combined organic eluate was evaporated to dryness to give a slightly orange liquid which was then distilled under vacuum to give 58.0 g (94percent) of the title product (b.p. 99-102 °C/11 mm Hg, ) as a colorless liquid crystallized overnight at room temperature.165 ml ( 413 mmol) of 2.5 M nBuLi in hexanes was added dropwise over 1 hto a solution of 82.2 g ( 400 mmol) of 3-chloro-4-bromo-toluene in 400 ml of THFcooled to -88°C. The resulting mixture was stirred for 30 min at this temperature, and then 44.0 g (602 mmol) ofDMF was added dropwise over 10 min by vigorousstirring. The reaction mixture was stirred overnight at room temperature, then cooled to ooc in an ice bath and then 100 ml of water and 400 ml of 3N HCl were added.The organic layer was separated and the aqueous layer was extracted with 2x 125 mlof dichloromethane. The combined organic extract was dried over K2C03 and thenpassed through a short layer of silica gel 60 ( 40-63 )liD). The silica gel layer wasadditionally washed with 50 ml of dichloromethane. The combined organic elute was evaporated to dryness to give a slightly orange liquid which was then distilled invacuum to give 58.0 g (94percent) ofthe title product (b.p. 99-102°C/11 mm Hg, ) as acolorless liquid that crystallized overnight at room temperature. Anal. calc. for C8H7Cl0: C, 62.15; H, 4.56. Found: C, 62.24; H, 4.45.1H NMR (CDCh): b 10.4 (s, 1H, CHO), 7.80 (d, J= 7.8 Hz, 1H, 6-H), 7.25(s, 1H, 3-H), 7.17 (d, J = 7.8 Hz, 1H, 5-H), 2.40 (s, 3H, 4-Me).

Molecular Weight:154.59
XLogP3:2.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:154.0185425
Monoisotopic Mass:154.0185425
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes