Acetyl chloride → HCID 15661017, compound
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:23]=[CH:22][C:21]2[O:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[CH:11]=1>ClCCCl>[C:5]([C:16]1[CH:17]=[CH:18][C:19]2[O:20][C:21]3[C:12](=[CH:11][C:10]([Br:9])=[CH:23][CH:22]=3)[S:13][C:14]=2[CH:15]=1)(=[O:7])[CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of aluminum chloride (1.2 g, 9 mmol) in 1,2-dichloro ethane (20 mL) at room temperature there was added acetyl chloride (0.57 mL, 628 mg, 8 mmol) and the mixture stirred for 10 minutes. There was added 2-bromophenoxathiin (J.A.C.S. 1936, 58, 717) (1.8 g, 6.4 mmol) and the mixture was stirred for 18 hours. After quenching with ice water, the organic portion was collected and the aqueous portion extracted with methylene chloride. The combined organic fractions, after washing 3 times with water and drying over MgSO4, were evaporated to a residue which on crystallization from methanol, followed by column chromatography on silica gel, eluting with a 1:5 mixture of ethyl acetate-hexane, gave the title product as a white solid (247 mg), m.p.: 143°-145° C.
Workup
- stirringthe mixture was stirred for 18 hours
- customAfter quenching with ice water
- customthe organic portion was collected
- extractionthe aqueous portion extracted with methylene chloride
- washThe combined organic fractions, after washing 3 times with water
- dry with materialdrying over MgSO4
- customwere evaporated to a residue which on crystallization from methanol
- washeluting with a 1:5 mixture of ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-d178460d36a341c2adbfd17288a75def
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05036067
Reaction notes
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