Benzyl mercaptan → 4-Fluorobenzenecarbodithioic acid phenylmethyl ester

HRID 990259Notes

Reaction equation

HRID 990259 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][CH:3]=1.[CH2:11]([SH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20]>C1(C)C=CC=CC=1>[CH2:11]([S:18][C:6](=[S:20])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 99734-Fluorobenzoic AcidHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 112770204-Fluorobenzenecarbodithioic acid phenylmethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-fluorobenzoic acid (1.40 g), benzyl mercaptan (1.24 g) and phosphorus pentasulfide (4.44 g) in toluene (40 ml) was refluxed for 12 h. A dark red color was developed immediately after heating. After the reaction was complete (as monitored by GC-MS), it was cooled to room temperature and purified by a column chromatography packed with neutral alumina, eluting with benzene. Removal of the solvent by distillation gave the single compound, benzyl-4-fluorodithiobenzoate (1.86 g, 71%). It was further characterized by 1H and 13C-NMR.

Workup

  1. temperaturewas refluxed for 12 h
  2. temperatureafter heating
  3. custompurified by a column chromatography
  4. washeluting with benzene
  5. customRemoval of the solvent
  6. distillationby distillation

Sources & evidence

ORD record
ord-c495ff45ce5b476d8d2f8edf8da25bce
Source dataset
uspto-grants-2002_10
Patent number
US06458968B2

Reaction notes

Loading…