2-Bromomethylnaphthalene → 2-Naphthalenemethanethiol

HRID 1631934Notes

Reaction equation

HRID 1631934 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.NC(N)=[S:15]>C(O)C>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][SH:15]

Participants

4

Reactant 2

HCID 703202-BromomethylnaphthaleneHCID 2723790Thiourea

Product 1

HCID 53142682-NaphthalenemethanethiolYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-(bromomethyl)naphthalene (10 g) in ethanol (40 ml) was added thiourea (3.79 g) and the reaction heated to reflux. After 6 h, the reaction was cooled in an ice bath, the precipitate was filtered off and washed with ice-cold ethanol. This was then added to NaOH solution (25%, 30 ml) and heated to reflux. After 2 h, the reaction was cooled to room temperature and water (200 ml) was added. The mixture was extracted with diethylether 3 times, the organic phase was separated, dried and concentrated to afford 5 g of the title compound.

Workup

  1. temperaturethe reaction heated to reflux
  2. temperaturethe reaction was cooled in an ice bath
  3. filtrationthe precipitate was filtered off
  4. washwashed with ice-cold ethanol
  5. additionThis was then added to NaOH solution (25%, 30 ml)
  6. temperatureheated to reflux
  7. waitAfter 2 h
  8. additionwater (200 ml) was added
  9. extractionThe mixture was extracted with diethylether 3 times
  10. customthe organic phase was separated
  11. customdried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-7ceeb46d22b443438a143df6a4f718e8
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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