Chloroacetyl chloride → 2-Chloro-1-(2-fluoro-4,6-dimethoxyphenyl)ethan-1-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([F:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:12][CH2:13][C:14](Cl)=[O:15].[Al+3].[Cl-].[Cl-].[Cl-]>ClC(Cl)C>[Cl:12][CH2:13][C:14]([C:6]1[C:7]([O:9][CH3:10])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[F:11])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution consisting of 3,5-dimethoxy fluorobenzene 26 (5.0 g, 32 mmol) and chloroacetyl chloride (4.3 g, 38 mmol) in dichloroethane (100 mL) was cooled to 0° C. and treated with AlCl3 (5.1 g, 38 mmol). The reaction was allowed to rt and stirred for 1 h and then washed with 2N HCl aq, brine, dried over MgSO4, filtered, concentrated and chromatographed on silica gel (1:9 EtOAc/hexanes to 2:8 EtOAc/hexanes) to yiled th product 27 (1.2 g) as a white solid: Mp 93-96° C.
Workup
- customwas allowed to rt
- washwashed with 2N HCl aq, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica gel (1:9 EtOAc/hexanes to 2:8 EtOAc/hexanes) to yiled th product 27 (1.2 g) as a white solid
Sources & evidence
- ORD record
- ord-c79011672fa04c26a0e262092493f46c
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06559177B2
Reaction notes
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