Trifluoroacetic acid → [4-(Bromomethyl)phenyl](cyclopentyl)acetic acid

HRID 877179Notes

Reaction equation

HRID 877179 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:28])[CH:14]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][Br:27])=[CH:22][CH:21]=1)[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[Br:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:13]([OH:28])=[O:12])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Product 1

HCID 21255101[4-(Bromomethyl)phenyl](cyclopentyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.635 ml (2.420 g, 21.228 mmol) of trifluoroacetic acid were added to a solution of 500 mg (1.415 mmol) of tert-butyl[4-(bromomethyl)phenyl](cyclopentyl)acetate (Example 10A) in 5 ml of dichloromethane. The mixture was stirred at room temperature for 2 h. Saturated aqueous sodium bicarbonate solution was then added, and the mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. This gave 364 mg (87% of theory) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf71743f68044443bc41ad3a928284c2
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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