Triethylamine → HCID 21075354, compound

HRID 1807856Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][O:10][CH3:11].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=O.[C:50]([O:53][CH2:54]C)(=[O:52])C>CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CO>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:50]([O:53][CH3:54])=[O:52])=[C:3]([CH2:9][O:10][CH3:11])[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Under an argon atmosphere, to a solution of 3.45 g of 1-bromo-4-fluoro-2-(methoxymethyl)benzene in 20 mL of dimethylsulfoxide were added 353 mg of palladium acetate, 650 mg of 1,3-bis(diphenylphosphino)propane, 4.4 mL of triethylamine, and 10 mL of methanol in this order, and the atmosphere in the reaction container were replaced with carbon monoxide, followed by stirring at 70° C. for 6 hours. The reaction mixture was poured into a mixed liquid of water and ethyl acetate. The aqueous layer was separated, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 1.75 g of methyl 4-fluoro-2-(methoxymethyl)benzoate.

Workup

customThe aqueous layer was separated
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f50bdf6dd6264dd09309f3bab55a16d0
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357688B2

Reaction notes

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