Benzyl Alcohol → Methyl 4-benzyloxycarbonyl-2-fluorobenzoate

HRID 2103812Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([F:27])[CH:18]=1.CN(C)[CH:30]=[O:31]>C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:8]([O:15][C:30]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([F:27])[CH:18]=1)=[O:31])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Palladium diacetate (4.5 mg, 0.02 mmol), 1,4-(bisdiphenylphosphino)butane (8.5 mg, 0.02 mmol), triethylamine (55.8 μL, 0.4 mmol) and benzyl alcohol (1 mL) were added to a solution of methyl 4-bromo-2-fluorobenzoate (46.6 mg, 0.2 mmol) in dimethylformamide (1 mL). In this solution, bubbling was carried out for a few minutes with carbon monoxide, and then this solution was heated at 120° C. for 12 hours under carbon monoxide atmosphere. After completion of the reaction, ethyl acetate was added, and the resultant product was washed with a saturated ammonium chloride aqueous solution, and purified with a silica gel column chromatography (hexane/ethyl acetate=19/1) to obtain 35.4 mg of the desired product as a yellow viscous liquid (yield 61%).

Workup

customIn this solution, bubbling
waitwas carried out for a few minutes with carbon monoxide
customAfter completion of the reaction, ethyl acetate
additionwas added
washthe resultant product was washed with a saturated ammonium chloride aqueous solution
custompurified with a silica gel column chromatography (hexane/ethyl acetate=19/1)

Sources & evidence

ORD record: ord-3d980ec6c8f842b18592b01d3bdc9607
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576115B2

Reaction notes

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