Carbon tetrabromide → 4-(Bromomethyl)-2-hydroxybenzonitrile

HRID 379024노트

반응식

HRID 379024 반응식
[OH:1][C:2]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>CN(C=O)C.C(Cl)Cl>[Br:32][CH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([OH:1])[CH:9]=1

참가 물질

6

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 216969742-Hydroxy-4-(hydroxymethyl)benzonitrile

생성물 1

HCID 216969934-(Bromomethyl)-2-hydroxybenzonitrile

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

2-Hydroxy-4-hydroxymethylbenzonitrile (0.20 g, 1.34 mmol) was dissolved in DMF (5 mL)—CH2Cl2(5 mL) and treated with triphenylphosphine (0.53 g, 2.01 mmol) and carbon tetrabromide (0.67 g, 2.01 mmol) at ambient temperature with stirring. After 2 h the reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL), the organic layer separated, dried (MgSO4), and filtered to give the title compound after silica gel chromatography (15% EtOAc/hexane to 25% EtOAc/hexane).

후처리

  1. customAfter 2 h the reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL)
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-8991a41115b445c2baca422ec49769a8
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297239B1

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