p-Toluenesulfonic acid → Ethyl 2-(4-bromophenyl)acetate

HRID 1525239Notes

Reaction equation

HRID 1525239 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 7020609Ethyl 2-(4-bromophenyl)acetateYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Bromophenylacetic acid, 7-c, (30 g, 0.14 mol) was dissolved in ethanol (150 mL) at reflux along with p-toluenesulphonic acid (2.4 g, 0.014 mol). The reaction mixture was then stirred overnight. The ethanol was the removed in vacuo and the residue was taken up in EA. Combined organic layers were washed with water and the aqueous layer was re-extracted with EA. Combined organic layers were then dried over Na2SO4 and concentrated to afford the titled compound, 12-a, (25 g, 74%). 1H NMR (300 MHz, CDCl3) δ 1.23-1.29 (m, 3H), 3.56 (s, 2H), 4.11-4.18 (m, 2H), 7.16 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H). LC-MS (M+H)+ 243, 245.

Workup

  1. customremoved in vacuo
  2. washCombined organic layers were washed with water
  3. extractionthe aqueous layer was re-extracted with EA
  4. dry with materialCombined organic layers were then dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ed6e4b3ebab4ace8b577741f9aab3f7
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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