Ethanol → Ethyl 2-(2-bromophenyl)acetate

HRID 1076566Notes

Reaction equation

HRID 1076566 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 two hours. The reaction mixture is heated under reflux for nine 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 nine 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-d0a90d00ca00483ab64a98496dd8f3c6
Source dataset
uspto-grants-1976_05
Patent number
US03957787

Reaction notes

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