4-Chlorobenzyl mercaptan → HCID 86588945, compound

HRID 2227609Notes

Reaction equation

HRID 2227609 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][SH:16])=[CH:13][CH:12]=1.[Na]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[CH:15]([S:16][CH:15](/[CH:9]=[CH:8]\[C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)[C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 804094-Chlorobenzyl mercaptanHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 5360545Sodium

Product 1

HCID 86588945HCID 86588945, compound

Procedure

A solution of 4-bromophenylacetylene (0.02 mol) and 4-chlorobenzyl mercaptan (0.02 mol) and metallic sodium (0.02 g atom) was subjected to the General Procedure to form Z-4-bromostyryl 4-chlorobenzylsulfide. The title compound was obtained in 87% yield following oxidation. 1HNMR (CDCl3) δ 4.58 (2H, s), 6.72 (1H, d, JH,H=12.08), 7.15-7.68 (8H aromatic+1H ethylenic).

Sources & evidence

ORD record
ord-5b4d4506b3b844d8a4df008a0f4a5b35
Source dataset
uspto-grants-2002_07
Patent number
US06414034B1

Reaction notes

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