2-Bromomethylnaphthalene → 2-Naphthalenemethanethiol
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
Product 1
Reagents, catalysts & solvents 1
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.