Boron tribromide → 3-Fluoro-4-hydroxybenzonitrile

HRID 626130

반응식

HRID 626130 반응식
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]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 27745483-Fluoro-4-methoxybenzonitrile

생성물 1

HCID 27829443-Fluoro-4-hydroxybenzonitrile수율 94.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dfd4485801a74d3e95fec146c510a0fd
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

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