1-(Bromomethyl)-3-chloro-2-fluorobenzene → (3-Chloro-2-fluorophenyl)methanethiol

HRID 2105146Notes

Reaction equation

HRID 2105146 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.NC(N)=[S:13]>C(O)C>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH2:5][SH:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 5228271-(Bromomethyl)-3-chloro-2-fluorobenzeneHCID 2723790Thiourea

Product 1

HCID 2761442(3-Chloro-2-fluorophenyl)methanethiolYield 89.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloro-2-fluorobenzyl bromide (1.00 g) and thiourea (0.35 g) were heated together at reflux in ethanol (10 ml) for 1 hour. The solvent was removed in-vacuo and the residue was suspended in 10% aqueous sodium hydroxide (10 ml) and heated at reflux for 3 hours. The solution was then acidified with conc. HCl and extracted into ether. Concentration of the organic phase in-vacuo gave the subtitle compound as a pale yellow oil (0.71 g).

Workup

  1. customThe solvent was removed in-vacuo
  2. temperatureheated
  3. temperatureat reflux for 3 hours
  4. extractionextracted into ether

Sources & evidence

ORD record
ord-a881e23498ba497399c228dc08ab9c20
Source dataset
uspto-grants-2009_08
Patent number
US07579342B2

Reaction notes

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