4-Fluorobenzoyl chloride → HCID 21182699, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)[S:8][C:7]=2[CH:25]=1.[Al+3].[Cl-].[Cl-].[Cl-].[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1>ClCCCl>[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([C:10]2[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][C:7]=3[S:8][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:15][CH:16]=2)=[O:36])=[CH:33][CH:32]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To 671.4 mg of 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophene (Example 1, Part B) in 10 mL of 1,2-dichloroethane was added 1.114 g of AlCl3 at 0° C., followed by dropwise addition of 0.30 mL of 4-fluorobenzoyl chloride. The deep red solution was stirred at 0° C. for 1 h and then at 0 to 15° C. for 19 h. The reaction was quenched by pouring the reaction mixture into 50 mL of ice-cold 2.0 N NaOH solution. The mixture was then extracted with 3×100 mL of EtOAc which was washed with 50 mL of H2O and brine. Combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography with 5 v/v % (10% conc NH4OH in MeOH) in CH2Cl2 to give 826.4 mg (92%) of the product ketone as viscous oil.
Workup
- waitat 0 to 15° C. for 19 h
- customThe reaction was quenched
- additionby pouring the reaction mixture into 50 mL of ice-cold 2.0 N NaOH solution
- extractionThe mixture was then extracted with 3×100 mL of EtOAc which
- washwas washed with 50 mL of H2O and brine
- dry with materialCombined organic layers were dried over MgSO4
- concentrationconcentrated
- custompurified by flash chromatography with 5 v/v % (10% conc NH4OH in MeOH) in CH2Cl2
Sources & evidence
- ORD record
- ord-7989afddb5224e21b6cde9a472157e43
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265575B1
Reaction notes
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