4-Bromo-2-chloro-6-methyl-benzoicacidmethylester

4-Bromo-2-chloro-6-methylbenzoic acid (1.10g, 4.41mmol) was dissolved in ethyl acetate (15mL). A solution of diazomethane in diethyl ether was added until the yellow colour persisted. After fifteen minutes the reaction was quenched with acetic acid. After one hour, the mixture was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated to provide the title compound as a yellow oil (1.31g, 113percent). To a solution of 4-bromo-2-chloro-6-methylbenzoic acid (3.500 g, 13.30 mmol) in anh. DMF (35 mL) at RTare added successively cesium carbonate (8.685 g, 26.70 mmol) and iodomethane (1.68 mL, 26.70 mmol) and the RM is stirred at RT for lh. Water and Et20 are added and the layers are separated. The aqueous layer is extracted twice with Et20 and the combined organic layers are washed with brine, dried over anh. MgSO4, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 7/3) affords methyl 4-bromo-2-chloro-6-methylbenzoate as a dark orange oil (3.450 g, 98percent). LC-MS B: tR = 0.99 mm; no ionization.To a solution of 4-bromo-2-chloro-6-methylbenzoic acid (3.500 g, 13.30 mmol) in anh. DMF (35 mL) at RT are added successively cesium carbonate (8.685 g, 26.70 mmol) and iodomethane (1.68 mL, 26.70 mmol) and the RM is stirred at RT for 1 h. Water and Et20 are added and the layers are separated. The aqueous layer is extracted twice with Et20 and the combined organic layers are washed with brine, dried over anh. MgSC>4, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 7/3) affords methyl 4-bromo-2-chloro-6-methylbenzoate as a dark orange oil (3.450 g, 98percent). LC-MS B: tR = 0.99 min; no ionization.C.1.49.5. (4-Bromo-2-chloro-6-methylphenyl)methanol To a cooled (-78°C) solution of To a cooled (-78°C) solution of To a cooled (-78°C) solution of To a solution of 4-bromo-2-chloro-6-methylbenzoic acid (3.500 g, 13.30 mmol) in anh. DMF (35 mL) at RT are added successively cesium carbonate (8.685 g, 26.70 mmol) and iodomethane (1.68 mL, 26.70 mmol) and the RM is stirred at RT for 1 h. Water and Et20 are added and the layers are separated. The aqueous layer is extracted twice with Et20 and the combined organic layers are washed with brine, dried over anh. MgSC>4, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 7/3) affords To a solution of

Molecular Weight:263.51
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:261.93962
Monoisotopic Mass:261.93962
Topological Polar Surface Area:26.3
Heavy Atom Count:13
Complexity:198
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes