Acetyl chloride → 3-Bromo-4-fluorophenyl acetate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[CH:3]=1)(=[O:19])[CH3:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of 3-bromo-4-fluorophenol (4.5 g, 23 mmol) [Ark Pharm, AK-26802] in dichloromethane (96 mL) at 0° C. was treated with triethylamine (4.9 mL, 35 mmol) followed by acetyl chloride (2.3 mL, 33 mmol) dropwise and stirred at 20° C. for 30 minutes. The reaction mixture was diluted with dichloromethane (100 mL), washed with 0.5 M hydrogen chloride in water (100 mL), saturated sodium bicarbonate (100 mL), and brine (50 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (5.5 g, quantitative) as a tan solid. This material, which did not ionize in the mass spectrometer, was used without further purification.
Workup
- washwashed with 0.5 M hydrogen chloride in water (100 mL), saturated sodium bicarbonate (100 mL), and brine (50 mL)
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-55f0749181e24305b17b2a0349b7a52e
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680108B2
Reaction notes
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