Benzyl 3,3-difluorocyclobutane-1-carboxylate → 3,3-Difluorocyclobutane-1-carboxylic acid

HRID 920773Notes

Reaction equation

HRID 920773 reaction equation
[F:1][C:2]1([F:16])[CH2:5][CH:4]([C:6]([O:8]CC2C=CC=CC=2)=[O:7])[CH2:3]1>C(O)C.[Pd]>[F:1][C:2]1([F:16])[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1

Participants

4

Reactant 1

HCID 56592986Benzyl 3,3-difluorocyclobutane-1-carboxylate

Product 1

HCID 137777893,3-Difluorocyclobutane-1-carboxylic acidYield 65.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 3,3-difluorocyclobutanecarboxylate (1.4 g, 6.2 mmol) in ethanol (50 mL) was added palladium on activated carbon (500 mg) and the reaction mixture was stirred at RT under an atmosphere of hydrogen (1 atm) for 12 h. The reaction mixture was filtered through a pad of CELITE® and the filtrate was concentrated to afford Intermediate 291A as pale yellow liquid (550 mg, 65% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.97-12.76 (m, 1H), 3.04-2.91 (m, 1H), 2.89-2.64 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a3d70355b97948f4a5658a443bdef9b6
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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