Methanol → Methyl 2-(2-bromophenyl)acetate

HRID 2206472Notes

Reaction equation

HRID 2206472 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:17])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 877542-Bromophenylacetic acid

Product 1

HCID 8063364Methyl 2-(2-bromophenyl)acetateYield 98%

Procedure

A solution of o-bromophenylacetic acid (5 g, 23.2 mmol) in dry methanol (40 mL) containing concentrated sulphuric acid (1 mL) was heated to reflux for 6 hours. The reaction mixture was cooled, then poured into ice water (100 mL) and extracted with ethyl acetate (30 mL×2). The organic layers were combined, washed successively with water (20 mL×2), saturated sodium bicarbonate solution (40 mL×2) and brine. And then the organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo to give methyl 2-(2-bromophenyl)acetate as a pale yellow liquid (5.2 g, 98%). 1H NMR (300 MHz, CDCl3): δ 7.57 (d, J=7.8 Hz, 1H), 7.34-7.22 (m, 2H), 7.17-7.11 (m, 1H), 3.80 (s, 2H), 3.72 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate (30 mL×2)
  5. washwashed successively with water (20 mL×2), saturated sodium bicarbonate solution (40 mL×2) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdd1e4555a914bba9ebd74433a723a1f
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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