Methanol → 2-[3-Fluoro-4-hydroxy-phenyl]-cyclopropanecarboxylic acid ethyl ester

HRID 62889Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([F:17])[CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br.CO>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([F:17])[CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

After 2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester (0.494 g, 2.07 mmol) obtained in Step B was dissolved in anhydrous DCM (7 mL), BBr3 1 M DCM solution (3 mL, 3.11 mmol) was added thereto at −78° C., and the mixture was stirred at room temperature for 3 hours. After the termination of the reaction, the reactant was added with MeOH, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/2) to obtain the title compound (0.424 g, 91%).

Workup

customAfter the termination of the reaction
concentrationconcentrated under reduced pressure
custompurified by column chromatography (eluent, EtOAc/Hex=1/2)

Sources & evidence

ORD record: ord-e91ce22eda65405f81aff1bdb27a793d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447044B2

Reaction notes

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