Acetic Acid → 2-Fluoro-5-hydroxybenzoic acid

HRID 714116

반응식

HRID 714116 반응식
[F:1][C:2]1C=[CH:8][C:7]([O:10]C)=[CH:6][C:3]=1C#N.[C:12]([OH:15])(=[O:14])[CH3:13]>Br.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:6][C:7]([OH:10])=[CH:8][C:13]=1[C:12]([OH:15])=[O:14]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 27745462-Fluoro-5-methoxybenzonitrile

생성물 1

HCID 27744802-Fluoro-5-hydroxybenzoic acid

시약·촉매·용매 2

HCID 260Hydrogen Bromide용매HCID 8857Ethyl Acetate용매

실험 절차

2-Fluoro-5-methoxybenzonitrile (3d, purchased from Alfa Aesar) (5 g, 33 mmol) was dissolved in hydrobromic acid (50 mL) and glacial acetic acid (30 mL), refluxed for 28 hours at 140° C., and then the reaction mixture was diluted with 100 mL ethyl acetate. The reaction mixture was then washed with 50 mL water and saturated sodium chloride solution successively for three times. The organic layers were combined and concentrated to give a crude product of 2-fluoro-5-hydroxybenzoic acid (3e), 2.88 g white solid (yield 56%). 1H NMR (600 MHz, DMSO-d6) δ 7.19-7.17 (m, 1H), 7.08-7.04 (m, 1H), 6.95-6.92 (m, 1H); ESI-MS m/z: calculated for 156.02. found 154.91 [M−H]+.

후처리

  1. washThe reaction mixture was then washed with 50 mL water and saturated sodium chloride solution successively for three times
  2. concentrationconcentrated

출처 및 근거

ORD 기록
ord-033fb64703a748a7b4d1e111c3f5a333
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187430B2

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