2,6-Dimethyl-4-bromobenzaldehyde

full text is not avalable from articleGeneral procedure: A solution of methyl 4-iodo-3-methylbenzoate (21 .7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -155C, /-PrMgCI (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2h at -155C and then warmed to 255C and allowed to react for an additional hour. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08 g. Yield: 80%). 1 H NMR (400 MHz, CDCI3) delta 10.35 (1 H, s), 8.00 (1 H, d, J=8Hz), 7.99 (1 H, s), 7.86 (1 H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) LC-MS: tR = 2.85 [M+H]+ = not ion. (method 3)General procedure: A solution of methyl 4-iodo-3-methylbenzoate (21 .7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -155C, /-PrMgCI (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2 h at -155C and then warmed to 255C and allowed to react for an additional hour. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08g .Yield: 80%). 1 H NMR (400 MHz, CDCI3) delta 10.35 (1 H, s), 8.00 (1 H, d, J=8Hz), 7.99 (1 H, s), 7.86 (1 H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) LC-MS: tR = 2.85 [M+H]+ = not ion (method 3).General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.2 mmol), glycine (0.2 mmol, 15.0 mg), Pd(OAc)2 (0.02 mmol, 4.5 mg), AgTFA (0.6 mmol, 132.8 mg) and 2 (0.3 mmol) under air. After addition of AcOH (2.0 mL) as solvent, TfOH (0.2 mmol, 30.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using petroleum ether as the eluent to afford the desired products.General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.24 mmol), glycine (0.1 mmol, 7.5 mg), Pd(OAc)2 (0.02 mmol, 4.45 mg), AgTFA (0.24 mmol, 53.01 mg) and 2 (0.2 mmol) under air. After addition of AcOH (2 mL) as solvent, TfOH (0.1 mmol, 15.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using PE as the eluent to afford the desired products.General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.24 mmol), glycine (0.1 mmol, 7.5 mg), Pd(OAc)2 (0.02 mmol, 4.45 mg), AgTFA (0.24 mmol, 53.01 mg) and 2 (0.2 mmol) under air. After addition of AcOH (2 mL) as solvent, TfOH (0.1 mmol, 15.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using PE as the eluent to afford the desired products.

Molecular Weight:213.07
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:211.98368
Monoisotopic Mass:211.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes