Thionyl Chloride → 2-Bromomethylbenzoyl chloride

HRID 1606897

Reaction equation

HRID 1606897 reaction equation
[Br:1][CH2:2][C:3]1[C:4]([C:9]([OH:11])=O)=[CH:5][CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:14])=O>C1C=CC=CC=1.CN(C=O)C>[Br:1][CH2:2][C:3]1[C:4]([C:9]([Cl:14])=[O:11])=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 3460032-(Bromomethyl)benzoic acid

Product 1

HCID 122516322-Bromomethylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

--A solution of α-bromotoluic acid (1.08 g) in dry benzene (10 ml) was stirred for 2 hours with thionyl chloride (0.73 ml) and dry DMF (five drops). The reaction mixture was evaporated to dryness, taken up in toluene and evaporated again. The crude product was crystallized from n-hexane (10 ml, charcoal) thereby obtaining pure α-bromotoluic acid chloride (0.95 g) as white flakes.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customevaporated again
  3. customThe crude product was crystallized from n-hexane (10 ml, charcoal)

Sources & evidence

ORD record
ord-a9975bce2bb948979e1ab38e7d6a5308
Source dataset
uspto-grants-1989_09
Patent number
US04863914

Linked notes

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