Methanol → 3-Bromo-5-(methoxymethyl)benzonitrile

HRID 539300노트

반응식

HRID 539300 반응식
[CH3:1][OH:2].[H-].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH2:14]Br)[CH:13]=1)[C:9]#[N:10]>CN(C=O)C>[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH2:14][O:2][CH3:1])[CH:13]=1)[C:9]#[N:10]

참가 물질

5

반응물 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 145678613-Bromo-5-(bromomethyl)benzonitrile

생성물 1

HCID 679793983-Bromo-5-(methoxymethyl)benzonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

MeOH (0.088 mL, 2.18 mmol) was added to a slurry of NaH (45 mg, 1.13 mmol) in DMF (2 mL). When gas evolution ceased, a solution of 3-bromo-5-(bromomethyl)benzonitrile (see WO2009/100169; 240 mg, 0.87 mmol) in DMF (1 mL) was added. The reaction was quenched by adding aq. sat NH4Cl solution. The mixture was partitioned between toluene (5 mL) and water (3 mL). The toluene layer was collected, washed with water, dried over Na2SO4, and concentrated in vacuo. The crude product was dried at reduced pressure and used in the next step: GCMS (CI) m/z 226 [M+H]+.

후처리

  1. customThe reaction was quenched
  2. additionby adding aq.
  3. customThe mixture was partitioned between toluene (5 mL) and water (3 mL)
  4. customThe toluene layer was collected
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. dry with materialThe crude product was dried at reduced pressure

출처 및 근거

ORD 기록
ord-d98aad59c86b4906be8b6d18461f753c
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865911B2

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