Boron tribromide → 3-Fluoro-4-hydroxybenzonitrile

HRID 626130

反応式

HRID 626130 の反応式
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14]C)[C:9]#[N:10]>ClCCl>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[C:9]#[N:10]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 27745483-Fluoro-4-methoxybenzonitrile

生成物 1

HCID 27829443-Fluoro-4-hydroxybenzonitrile収率 94.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

BBr3 (20 mL, 0.211 mol) was added to 3-fluoro-4-methoxybenzonitrile (15.6 g, 0.103 mol) in dichloromethane (100 mL) at 0° C. The mixture was refluxed for 3 days under a nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with dichloromethane. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure gave 13.3 g (94%) of the product as a gray solid. 1H NMR (400 MHz, CDCl3) δ 7.38-7.42 (m, 2H), 7.09 (dd, J=8.8 Hz, 8.4 Hz, 1H), 5.68 (s, 1H).

後処理

  1. temperatureThe mixture was refluxed for 3 days under a nitrogen atmosphere
  2. customThe reaction mixture was quenched with ice water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation under reduced pressure

出典と根拠

ORDレコード
ord-dfd4485801a74d3e95fec146c510a0fd
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

関連ノート

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