Methanol → HCID 59627720, compound

HRID 1930180Notes

Reaction equation

BrB(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([C:15]2([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16]2)[CH:9]=[C:10]([F:14])[C:11]=1[O:12]C.CO>ClCCl>[F:5][C:6]1[CH:7]=[C:8]([C:15]2([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17]2)[CH:9]=[C:10]([F:14])[C:11]=1[OH:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Tribromoborane (0.666 ml, 7.04 mmol) was added dropwise to methyl 1-(3,5-difluoro-4-methoxyphenyl)cyclopropanecarboxylate (Intermediate 28-4; 1.4216 g, 5.87 mmol) in dichloromethane (46.2 mL) at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 1 hour. The reaction mixture was added dropwise to methanol (11.87 mL, 293.45 mmol) (care reaction is vigorous and exothermic—MeOH kept in ice bath) and the mixture was stirred for a further 20 minutes. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL), and washed sequentially with saturated NaHCO3 (50 mL) and water (50 mL). The organic layer was dried with MgSO4 and evaporated to afford crude product. The crude product was purified by flash silica chromatography, eluted at 25% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 1-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylate (0.657 g, 49.1%) as a white solid.

Workup

stirringthe mixture was stirred for a further 20 minutes
customThe reaction mixture was evaporated to dryness
dissolutionredissolved in DCM (50 mL)
washwashed sequentially with saturated NaHCO3 (50 mL) and water (50 mL)
dry with materialThe organic layer was dried with MgSO4
customevaporated
customto afford crude product
customThe crude product was purified by flash silica chromatography
washeluted at 25% EtOAc in isohexane
customPure fractions were evaporated to dryness

Sources & evidence

ORD record: ord-7d200a76acbb41dd9ea6d2a2e8c90a34
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188092B2

Reaction notes

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