Ethanol → Ethyl 2-(2-bromophenyl)acetate

HRID 440577Notes

Reaction equation

HRID 440577 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:16][CH3:17])=[O:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 877542-Bromophenylacetic acid

Product 1

HCID 2780092Ethyl 2-(2-bromophenyl)acetate

Procedure

43.0 g (0.2 mol) of DL-2-bromo-phenylacetic acid are dissolved in 400 ml of ethanol at ambient temperature with stirring. At 5°-10° C. 11.8 g (0.2 mol) of thionylchloride are slowly added dropwise whilst cooling with ice. After 12 hours at ambient temperature the solvent is distilled off and the residue is taken up in ethyl acetate. After extraction with saturated sodium bicarbonate solution and saturated saline solution the product is dried over sodium sulphate and evaporated down.

Workup

  1. customAt 5°-10° C
  2. temperaturewhilst cooling with ice
  3. distillationAfter 12 hours at ambient temperature the solvent is distilled off
  4. extractionAfter extraction with saturated sodium bicarbonate solution and saturated saline solution the product
  5. dry with materialis dried over sodium sulphate
  6. customevaporated down

Sources & evidence

ORD record
ord-0cec23d3f533451ca72c0bf6b6485f20
Source dataset
uspto-grants-1996_05
Patent number
US05519138

Reaction notes

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