Methyl 2-bromo-4-carbamoylbenzoate → Methyl 2-bromo-4-cyanobenzoate

HRID 1037123노트

반응식

HRID 1037123 반응식
[Br:1][C:2]1[CH:11]=[C:10]([C:12](=O)[NH2:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

3

반응물 1

HCID 86685485Methyl 2-bromo-4-carbamoylbenzoate

생성물 1

HCID 23076848Methyl 2-bromo-4-cyanobenzoate수율 90.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 2-bromo-4-carbamoylbenzoate (1.3 g, 5.06 mmol) in dry DMF (20 mL) was added (CNCl)3 (1.85 g, 10.12 mmol) at rt and then stirred at rt for 3 h. The reaction mixture was quenched with water and extracted with EA (100 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give crude methyl 2-bromo-4-cyanobenzoate as a white solid (1.1 g). It was used without further purification. 1H NMR (400 MHz, CDCl3): δ 8.36 (s, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.91 (d, J=8.0 Hz, 1H), 3.90 (s, 3H) ppm.

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EA (100 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-37ccfc63b4234999a20c0337debaf99b
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

반응 노트

불러오는 중…