Hydrochloric Acid → Perfluorophenyl 4-bromobutanoate
Reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[Br:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18].CCN=C=NCCCN(C)C.Cl.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[C:7]([O:8][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][Br:13])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of pentafluorophenol (3.3 g, 17.96 mmol), 4-bromobutanoic acid (3.0 g, 17.96 mmol) and DMAP (0.440 g, 3.59 mmol) in CH2Cl2 (30 ml), cooled to 0° C., EDAC.HCl (5.2 g, 26.94 mmol) was added in portion. The mixture was then stirred at 0° C. for 30 minutes. Then it was gradually warmed to room temperature and stirred for 480 minutes. Then the mixture was diluted with NaH2PO4 aqueous (5%, 50 ml) and acidified with HCl 1N to pH 3-4. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (2×50 ml). The organic phase washed with brine, dried over Na2SO4 and evaporated to give an oil that was purified by flash chromatography (n-Hexane/EtOAc 98:2) to yield 4-bromobutanoic acid pentafluorophenyl ester (5.2 g, 86%) as a colorless oil.
Workup
- temperatureThen it was gradually warmed to room temperature
- stirringstirred for 480 minutes
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with CH2Cl2 (2×50 ml)
- washThe organic phase washed with brine
- dry with materialdried over Na2SO4
- customevaporated
- customto give an oil that
- customwas purified by flash chromatography (n-Hexane/EtOAc 98:2)
Sources & evidence
- ORD record
- ord-d42e38b986a94bdfb04dffe0f99d8d98
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723529B2
Reaction notes
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