Hydrochloric Acid → Methyl 2-(3-bromophenyl)acetate

HRID 1717671Notes

Reaction equation

HRID 1717671 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.Cl.[CH3:13]O>>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetateYield 96%

Conditions

Temperature
58 °C

Procedure

3-bromophenylacetic acid (10000 mg, 46.50 mmol) was dissolved in methanol (200 mL) at room temperature and concentrated hydrochloric acid (4 mL) was added. The resulting solution was heated at 58° C. for 2 h then cooled to room temperature at which time the volatiles were removed in vacuo. The crude material was dissolved in ethyl acetate and the solution was carefully poured into a saturated aqueous sodium bicarbonate solution. The phases were separated and the combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by MPLC (Biotage) with a gradient of 4 to 35% AcOEt/hexanes to give (3-bromo-phenyl)-acetic acid methyl ester as a colorless oil (10250 mg, 96%). GC-MS (MH+230 RT=9.34 min).

Workup

  1. temperaturethen cooled to room temperature at which time the volatiles
  2. customwere removed in vacuo
  3. dissolutionThe crude material was dissolved in ethyl acetate
  4. additionthe solution was carefully poured into a saturated aqueous sodium bicarbonate solution
  5. customThe phases were separated
  6. dry with materialthe combined organic extracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by MPLC (Biotage) with a gradient of 4 to 35% AcOEt/hexanes

Sources & evidence

ORD record
ord-e77b37a9593949b1a53a4ad156a74e26
Source dataset
uspto-grants-2010_09
Patent number
US07803956B2

Reaction notes

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