Methyl 3-bromobenzoate → HCID 20601397, compound
Reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:35]1[CH:36]=[C:37]([CH:42]=[CH:43][CH:44]=1)[C:38]([O:40][CH3:41])=[O:39]>CN(C)C=O.[Pd](Cl)Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH3:41][O:40][C:38]([C:37]1[CH:36]=[C:35]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=2)[CH:44]=[CH:43][CH:42]=1)=[O:39]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2.0 g (9.85 mmol.) 4-bromo-2-fluorobenzaldehyde, 2.8 g (10.8 mmol.) bis(pinacolato)diboron, 2.9 g (29.6 mmol.) potassium acetate and 216 mg (0.3 mmol.) bis(diphenylphosphino)ferrocene palladium dichloride in 60 mL dimethylformamide was heated at 80° C. for 4 hours. The mixture was cooled and 4.2 g (19.7 mmol.) methyl 3-bromobenzoate and 216 mg (0.3 mmol.) bis(diphenylphosphino)ferrocene palladium dichloride was added and the mixture heated at 80° C. for 18 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were combined then washed successively with 1N NaOH, 1N HCl, water, brine then dried (MgSO4) and concentrated in vacuo to give an oil. Chromatography on Silica Gel eluting with ethyl acetate/hexanes (1:5) gave 1.4 g 3′-fluoro-4′-formyl-biphenyl-3-carboxylic acid methyl ester as an oil.
Workup
- temperatureThe mixture was cooled
- temperaturethe mixture heated at 80° C. for 18 hours
- extractionextracted with ethyl acetate
- washThe ethyl acetate extracts were combined then washed successively with 1N NaOH, 1N HCl, water, brine
- dry with materialthen dried (MgSO4)
- concentrationconcentrated in vacuo
- customto give an oil
Sources & evidence
- ORD record
- ord-aec28bd035254546b1de2590206c5ac9
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06953810B2
Reaction notes
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