Pentafluorophenol → Perfluorophenyl 4-bromobutanoate

HRID 2241106Notes

Reaction equation

HRID 2241106 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[F:8][C:9]1[C:14](O)=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=1[F:19]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:8][C:9]1[C:14]([O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][Br:1])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=1[F:19]

Participants

5

Reactant 2

HCID 13041PentafluorophenolHCID 758094-Bromobutyric acid

Product 1

HCID 86025169Perfluorophenyl 4-bromobutanoateYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobutyric acid (0.91 g, 5.4 mmol), pentafluorophenol (1.00 g, 5.4 mmol) and DMAP (0.13 g, 1.1 mmol) in CH2Cl2 (10 ml) cooled to 0° C. under nitrogen, N,N-dicyclohexylcarbodiimide (1.70 g, 8.1 mmol) was added in portions. After 1 h the reaction was slowly warmed to room temperature and stirred for 5 hours. The dicyclohexylurea was filtered off and the mother liquor was concentrated and purified by flash chromatography (n-Hexane/EtOAc 98:2) affording 4-bromobutyric acid pentafluorophenyl ester as a colourless oil (1.40 g, 78%). A mixture of 4-bromobutyric acid pentafluorophenyl ester (0.65 g, 1.9 mmol) and AgNO3 (0.83 g, 4.9 mmol) in CH3CN (8 ml) was warmed at 70° C. for 20 minutes at the microwave. The formed salts were filtered off, the solvent was concentrated and the residue purified by flash chromatography (n-Hexane/EtOAc 95:5) affording 4-nitrooxybutyric acid pentafluorophenyl ester as a clear oil (0.38 g, 62%).

Workup

  1. filtrationThe dicyclohexylurea was filtered off
  2. concentrationthe mother liquor was concentrated
  3. custompurified by flash chromatography (n-Hexane/EtOAc 98:2)

Sources & evidence

ORD record
ord-92d19c2ca2c649718b804d189709deb7
Source dataset
uspto-grants-2010_05
Patent number
US07723529B2

Reaction notes

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