Bromine → 4-(2-bromoacetyl)benzenesulfonyl Chloride
Reaction equation
[BrH:1].Cl[C:3]1[CH:8]=[CH:7][C:6](C2(O)CSC(=NC)N2C)=[CH:5][C:4]=1[S:18]([Cl:21])(=[O:20])=[O:19].ClC1C=C[C:26]([C:29](=[O:31])C)=CC=1S(Cl)(=O)=O.BrBr>C(OCC)(=O)C>[Br:1][CH2:26][C:29]([C:7]1[CH:8]=[CH:3][C:4]([S:18]([Cl:21])(=[O:19])=[O:20])=[CH:5][CH:6]=1)=[O:31]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(4-Chloro-3-chlorosulfonylphenyl-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide. 5.1 g of 4'-chloro-3'-chlorosulfonyl-acetophenone were reacted in the manner described in Example 1(a) with 3.2 g bromine in ethyl acetate to yield the 2-bromo-4'-chlorosulfonylacetophenone (melting point: 111° C. from chloroform, γC=O 1700 cm-1) which was reacted without further isolation, as described in Example 1(b) with 2.1 g of 1,3-dimethylthiourea in 50 ml of acetone. The mixture was stirred for 30 minutes at 30°-35° C., cooled to 10° C. and the 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-methylimino-1,3-thazolidine-4-ol-hydrobromide was filtered. Colorless crystals melting at 162° C. (decomposition).
Sources & evidence
- ORD record
- ord-ea0ce2ff787c4b74bce84ce6f54f7a7b
- Source dataset
- uspto-grants-1978_11
- Patent number
- US04125614
Reaction notes
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