Ethanol → [1-(4-Bromo-phenyl)-cyclopropyl]-acetic acid ethyl ester

HRID 1183328Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:20][CH2:21]O>>[CH2:20]([O:13][C:12](=[O:14])[CH2:11][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1)[CH3:21]

Participants

Reactant 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 665776222-[1-(4-Bromophenyl)cyclopropyl]acetic acid

Product 1

HCID 66577718[1-(4-Bromo-phenyl)-cyclopropyl]-acetic acid ethyl ester

Conditions

Temperature: 80 °C

Procedure

[1-(4-Bromo-phenyl)-cyclopropyl]-acetic acid (from the previous step) was dissolved in EtOH (80 mL) and conc. H2SO4 (2 mL) was added. The reaction was heated to 80° C. overnight then concentrated and submitted to standard aqueous workup to afford the title compound.

Workup

concentrationthen concentrated

Sources & evidence

ORD record: ord-603146772fe34e7e816b5673d55d91b2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664220B2

Reaction notes

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