Triethylamine → p-BROMOPHENYL 1-(p-CHLOROPHENYLSULFONYL)VINYL SULFIDE

HRID 1156385Notes

Reaction equation

HRID 1156385 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:10]Cl)=[CH:4][CH:3]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([C:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH2:10])(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 130448002-CHLORO-1-(p-CHLOROPHENYLSULFONYL)ETHYL p-BROMOPHENYL SULFIDE

Product 1

HCID 13044811p-BROMOPHENYL 1-(p-CHLOROPHENYLSULFONYL)VINYL SULFIDEYield 40.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thirty-five grams (82 mmoles) of 2-chloro-1-(p-chlorophenylsulfonyl)ethyl p-bromophenyl sulfide was dissolved in 100 ml of tetrahydrofuran and treated with 12 ml (86 mmoles) of triethylamine. The mixture was diluted with 100 ml of diethyl ether and allowed to stand for 15 minutes. The precipitated triethylamine hydrochloride was separated by filtration. Evaporation of solvent from the filtrate gave 35 g of crude solid m.p. 45°-95°. Recrystallization from 100 ml of ethyl acetate-pentane (45:55) gave 13 g of pure product, m.p. 97°-99°.

Workup

  1. customThe precipitated triethylamine hydrochloride was separated by filtration
  2. customEvaporation of solvent from the filtrate
  3. customgave 35 g of crude solid m.p. 45°-95°
  4. customRecrystallization from 100 ml of ethyl acetate-pentane (45:55)

Sources & evidence

ORD record
ord-eb4557c5d75a4e4ab7e7818c24cc9fc8
Source dataset
uspto-grants-1982_06
Patent number
US04335142

Reaction notes

Loading…