Hydrochloric Acid → (3,4-difluorophenyl)methanethiol

HRID 1455011Notes

Reaction equation

HRID 1455011 reaction equation
N[C:2](N)=[S:3].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[F:14])CBr.Cl>C(O)C.[OH-].[Na+]>[F:5][C:6]1[CH:7]=[C:8]([CH2:2][SH:3])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 2723790Thiourea

Product 1

HCID 2761428(3,4-difluorophenyl)methanethiol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Thiourea (5.0 g) was added to a solution of 3,4-difluorobenzyl bromide (13.6 g) in ethanol (100 ml). The mixture was heated at reflux for 3 h before removal of the volatiles in vacuo. The crude solid was suspended in aqueous sodium hydroxide solution (1.6M, 110 ml) and heated at reflux for 3 h before allowing to cool to room temperature. The reaction was acidified with concentrated hydrochloric acid and the organics extracted with ether (200 ml). The organic layer was washed with saturated sodium bicarbonate solution (2×50 ml), brine (20 ml), dried (MgSO4), and concentrated in vacuo to provide the subtitle product as a colourless oil. Yield 11.1 g

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h before removal of the volatiles in vacuo
  3. temperatureheated
  4. temperatureat reflux for 3 h
  5. extractionthe organics extracted with ether (200 ml)
  6. washThe organic layer was washed with saturated sodium bicarbonate solution (2×50 ml), brine (20 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09df2e4c3698490e81152dac35327843
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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