Reaction #334246

Reaction equation

4-Mercaptobenzyl alcohol

bromochloromethane

triethylamine

→

4-(Chloromethylthio) benzyl alcohol

Conditions

Workup

1. 1
   Washwashed with water
2. 2
   Dryingthe dried (MgSO4) organic solution
3. 3
   Otherevaporated
4. 4
   Otherto leave the product
5. 5
   Otherno further purification for use in Example 33

Procedure

4-Mercaptobenzyl alcohol (see J.Chem.Soc 1963 p 1947) (5.0 mmol) was dissolved in bromochloromethane (100 mmol) and triethylamine (5 mmol) added dropwise. The resultant mixture was stirred for 1 hour at room temperature, washed with water and the dried (MgSO4) organic solution evaporated to leave the product. Yield 0.94g (95%) 1H NMR (CDCl3, δ): 2.03 (OH), 4.65 (CH2O), 4.90 (CH2S), 7.1-7.4 (Ph). The product needed no further purification for use in Example 33.

Source