Triethylamine → HCID 21075354, compound

HRID 1396663Notes

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

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

Sources & evidence

ORD record: ord-f7a70c10310f4255be7ead246593d315
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901126B2

Reaction notes

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