Trifluoroacetic acid → 2-(2-Fluorophenyl)cyclopropane-1-carboxylic acid

HRID 1351582Notes

Reaction equation

HRID 1351582 reaction equation
C([O:5][C:6]([C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:9]1[CH2:10][CH:8]1[C:6]([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58635344(R,R)-2-(2-Fluoro-phenyl)-cyclopropanecarboxylic acid tert-butyl ester

Product 1

HCID 218646742-(2-Fluorophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the t-butyl ester from Step 1 (0.52 g, 0.0022 mole) in dichloromethane at 0° C. was added trifluoroacetic acid and the mixture stirred at rt for 30 min. The reaction was concentrated in vacuo to give the title compound as an oil. Analysis of the acid by chiral HPLC (Chirapak AD, 250×4.6 mm) using 95/5(A/B), 0.2% trifluroacetic acid in hexane(A) and ethanol(B), 1 mL/min, showed the material to have a purity of ≧94% EE. M.S. (M+1): 181.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-5350bd81a11b41eaacdc35aa7d7fb552
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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