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

HRID 1097354Notes

Reaction equation

HRID 1097354 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 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-chloro-2-fluorobenzylbromide (5.0 g), thiourea (3.4 g) in a solvent of ethanol (200 ml) was heated under reflux for 16 hours. The mixture was evaporated to dryness and to the residue was added a solution of sodium hydroxide (30 g) in water (300 ml) and the mixture heated under reflux for 1 hour. Allowed to cool to room temperature and acidified with concentrated hydrochloric acid, the product was extracted into ether to give the subtitle compound as an oil (2.51 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe mixture was evaporated to dryness and to the residue
  4. additionwas added a solution of sodium hydroxide (30 g) in water (300 ml)
  5. temperaturethe mixture heated
  6. temperatureunder reflux for 1 hour
  7. extractionthe product was extracted into ether

Sources & evidence

ORD record
ord-d25d4a2e52cc4e399a068e7fa00a04db
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

Loading…