Acetonitrile → Benzene, 1-chloro-4-[[(4-nitrophenyl)methyl]thio]-
Reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][Si](C)(C)C)=[CH:15][CH:14]=1.C(#N)C>CN(C)P(=O)(N(C)C)N(C)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][S:19][C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
Procedure
1.50 g (7.0 mmoles) of 4-nitrobenzyl bromide was added to a mixture of 1.36 g (6.3 mmoles) of 4-chlorophenylthio(trimethyl)silane, 20 ml of acetonitrile and 2.3 ml of hexamethylphosphoric triamide and the conversion was complete after stirring for 5 minutes at room temperature. The reaction mixture was evaporated to dryness and the residue was dissolved in 50 ml of ethyl acetate. The solution was washed sequentially with water (twice 10 ml), 10 ml of a 1N KOH solution and water (twice 10 ml), dried and evaporated to dryness. The solid residue was washed with heptane on a sintered glass filter and the crystals obtained were vacuum dried at room temperature to obtain 1.67 g (95% yield) of 4-chlorophenyl 4-nitrobenzyl sulfide melting at 66°-68° C.
Workup
- customThe reaction mixture was evaporated to dryness
- dissolutionthe residue was dissolved in 50 ml of ethyl acetate
- washThe solution was washed sequentially with water (twice 10 ml), 10 ml of a 1N KOH solution and water (twice 10 ml)
- customdried
- customevaporated to dryness
- washThe solid residue was washed with heptane on a sintered glass
- filtrationfilter
- customthe crystals obtained
- customdried at room temperature
Sources & evidence
- ORD record
- ord-983cff6a0033446b99eeff8b2b7340d6
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04496720
Reaction notes
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