Methyl 3-bromo-5-fluorobenzoate

To a solution of 3-bromo-5-fluorobenzoic acid (2 g, 9.13 mmol) in DCM/ MeOH (20 ml/ 5 ml) is added trimethylsilyldiazomethane (2M solution in ether; 1 eq, 9.13 mmol) and the mixture is stirred for 1 h. Acetic acid was added dropwise until the yellow colour disappeared. The solvents are then removed in vacuo. The residue is dissolved in DCM and washed with KCommercially available 3-bromo-5-fmorobenzoic acid (1.Og, 4.57 mmol) was dissolved in methylene chloride (20 mL) trimethylsilyl diazomethane (2M solution in hexane) (5 mL, 10 mmol) was added and the reaction mixture was stirred for 30 min. at room temperature. The reaction mixture was concentrated and purified by silica gel chromatography (hexane/methylene chloride 2:1) to yield A101.1 (229mg, 21percent).Intermediate 25: Methyl 3-bromo-5-fluorobenzoate A mixture of 3-bromo-5-fluorobenzoic acid (2.8 g, 13.0 mmol) and thionyl chloride (10 mL) was heated to 70 °C for 2 h, after cooling to room temperature excess thionyl chloride was evaporated. To the residue at 0 °C was methanol (50 mL) and triethylamine (4.5 mL) added, the reaction was stirred at 0°C for 5 minutes and then at room temperature for 2 h. The mixture was concentrated, diluted with ethyl acetate (100 mL) and washed consecutively with: 1) hydrochloric acid (5percent, 50 mL), 2) saturated sodium bicarbonate (50 mL), the organic phase was dried over magnesium sulfate and evaporated. Purification by flash chromatography using heptane:ethyl acetate 9:1 as the eluent gave the title compound (1.8 g, 60percent). H NMR (400 MHz, CDClStep 1: Preparation of methyl 3-bromo-5-fluoro-benzoate To a solution of 3-bromo-5-fluorobenzoic acid (10.0 g, 45.7 mmol) in MeOH (100 mL) was added SOClUnder argon protection, The reaction flask was added benzophenone hydrazone (2.2g, 11.2mmol), Palladium acetate (0.11 g, 0.5 mmol), 2, 2-bis-(diphenylphosphino)-1, 1-binaphthyl (0.3 g, 0.5 mmol), toluene (15 mL), Heat to 100 C and stir for 3 minutes. Cool to room temperature, To the reaction flask was added

Molecular Weight:233.03
XLogP3:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:231.95352
Monoisotopic Mass:231.95352
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes