Bromochloromethane → 4-(Chloromethylthio) benzyl alcohol

HRID 247064Notes

Reaction equation

HRID 247064 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.Br[CH2:11][Cl:12].C(N(CC)CC)C>>[Cl:12][CH2:11][S:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6333BromochloromethaneHCID 8471TriethylamineHCID 4677905(4-Sulfanylphenyl)methanol

Product 1

HCID 538676354-(Chloromethylthio) benzyl alcohol

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.

Workup

  1. washwashed with water
  2. dry with materialthe dried (MgSO4) organic solution
  3. customevaporated
  4. customto leave the product
  5. customno further purification for use in Example 33

Sources & evidence

ORD record
ord-0b078959122b4c1ead27ab20e7cc57cb
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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