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

HRID 29254

反応式

HRID 29254 の反応式
[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

参加物

4

反応物 3

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

生成物 1

HCID 11746402Methyl 2-(3-bromophenyl)acetate収率 96%

反応条件

温度
58 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e2b03e85c69545fe817a9caa44377c00
出典データセット
uspto-grants-2008_09
特許番号
US07420066B2

関連ノート

読み込み中…