Ethanol → Ethyl 2-(2-bromophenyl)acetate

HRID 1414210Notes

Reaction equation

HRID 1414210 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#N.S(=O)(=O)(O)[OH:12].[CH2:16]([OH:18])[CH3:17]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:18][CH2:16][CH3:17])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 296252-Bromobenzyl cyanide

Product 1

HCID 2780092Ethyl 2-(2-bromophenyl)acetate

Procedure

To a cooled solution of 730.0 g of o-bromophenylacetonitrile in 2.9 l of absolute ethanol is added, dropwise, while stirring, 740 ml of concentrated sulphuric acid. The addition requires about 2 hours. The reaction mixture is heated under reflux for 9 hours, poured into ice water, and extracted with 2.5 l of ether. The ether extracts are washed, dried, and concentrated. The residue is distilled to give 780.0 g of ethyl o-bromophenylacetate, bp. about 115°-117° (4mm), nD26 1,5434.

Workup

  1. additionThe addition
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 9 hours
  4. extractionextracted with 2.5 l of ether
  5. washThe ether extracts are washed
  6. customdried
  7. concentrationconcentrated
  8. distillationThe residue is distilled

Sources & evidence

ORD record
ord-48355715b1c14684b929111462e6fbf1
Source dataset
uspto-grants-1977_01
Patent number
US04001233

Reaction notes

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