Methanol → [2-(3-Fluoro-4-hydroxy-phenyl)-cyclopropyl]-acetic acid methyl ester

HRID 62901Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:13]=[CH:12][C:11]([O:14]C)=[C:10]([F:16])[CH:9]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([F:16])[CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

After [2-(3-fluoro-4-methoxy-phenyl)-cyclopropyl]-acetic acid methyl ester (0.067 g, 0.28 mmol) obtained in Step E was dissolved in anhydrous DCM (2 mL), BBr3 1M DCM solution (0.42 mL, 0.42 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 then purified by column chromatography (eluent, EtOAc/Hex=1/2) to obtain the title compound (0.053 g, 84%).

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-c5c7a486972b40ad8415f97c076b81af
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447044B2

Reaction notes

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