Ethanol → Ethyl 3-(bromophenyl)acetate

HRID 1910473Notes

Reaction equation

HRID 1910473 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-c93a0975a5524f1191c0495959325408
Source dataset
uspto-grants-2013_12
Patent number
US08604016B2

Reaction notes

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