Ethanol → Ethyl 3-(bromophenyl)acetate

HRID 538097Notes

Reaction equation

HRID 538097 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12][CH2:13]O>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11470552Ethyl 3-(bromophenyl)acetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 2-(3-bromophenyl)acetic acid 1103 (10.0 g, 46.5 mmol) in 100 mL EtOH was added conc. H2SO4 (10 drops) and the mixture heated to relux temperature for 3 hours. The mixture was allowed to cool to room temperature and the volatiles were removed under reduced pressure. The residue was taken up in EtOAc (100 mL) and washed with water (2×50 mL), saturated NaHCO3 (1×25 mL), brine (2×25 mL) and dried over Na2SO4. The Na2SO4 was removed by filtration and the volatiles removed under reduced pressure to give ethyl 2-(3-bromophenyl)acetate 1097 (11.1 grams) as a liquid). 1H NMR 300 MHz CDCl3: δ 7.41 (m, 2H), 7.20 (m, 2H), 4.14 (q, 2H, J=9.5 Hz), 3.57 (s, 2H), 1.25 (t, 3H, J=9.5 Hz).

Workup

  1. temperaturethe mixture heated
  2. customfor 3 hours
  3. customthe volatiles were removed under reduced pressure
  4. washwashed with water (2×50 mL), saturated NaHCO3 (1×25 mL), brine (2×25 mL)
  5. dry with materialdried over Na2SO4
  6. customThe Na2SO4 was removed by filtration
  7. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-8b4f435480824361a672da04094cbb75
Source dataset
uspto-grants-2014_10
Patent number
US08865718B2

Reaction notes

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