Acetic Acid → 2-Fluoro-5-hydroxybenzoic acid

HRID 714116ノート

反応式

HRID 714116 の反応式
[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]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 27745462-Fluoro-5-methoxybenzonitrile

生成物 1

HCID 27744802-Fluoro-5-hydroxybenzoic acid

試薬・触媒・溶媒 2

HCID 260Hydrogen Bromide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-033fb64703a748a7b4d1e111c3f5a333
出典データセット
uspto-grants-2015_11
特許番号
US09187430B2

反応ノート

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