p-Fluorotoluene-alpha-thiol → Z-4-fluorostyryl 4-fluorobenzylsulfide

HRID 431154Notes

Reaction equation

HRID 431154 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][SH:16])=[CH:13][CH:12]=1.[Na]>>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[CH:15]([S:16][CH:8](/[CH:9]=[CH:8]\[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:14]2[CH:17]=[CH:18][C:11]([F:10])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 85171p-Fluorotoluene-alpha-thiolHCID 5226271-Ethynyl-4-fluorobenzeneHCID 5360545Sodium

Product 1

HCID 86588943Z-4-fluorostyryl 4-fluorobenzylsulfide

Procedure

A solution of 4-fluorophenylacetylene (0.02 mol) and 4-fluorobenzyl mercaptan (0.02 mol) and metallic sodium (0.02 g atom) was subjected to Procedure 2 to form (Z)-4-fluorostyryl 4-fluorobenzylsulfide. The title compound was obtained in 78% yield following oxidation. 1HNMR (CDC13) δ4.60 (2H, s), 6.65 (1H, d, JH,H=11.83), 7.20-7.65 (8H aromatic+1H ethylenic).

Sources & evidence

ORD record
ord-07eec70903ad40c7b5cb75c7b04bf834
Source dataset
uspto-grants-2003_12
Patent number
US06656973B2

Reaction notes

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