Stannous Chloride → Methyl 3-amino-5-bromobenzoate

HRID 852529

반응식

HRID 852529 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([Br:13])[CH:5]=1.Cl[Sn]Cl>CO>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([Br:13])[CH:7]=[C:8]([NH2:10])[CH:9]=1

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 239341Methyl 3-bromo-5-nitrobenzoate

생성물 1

HCID 18763420Methyl 3-amino-5-bromobenzoate수율 93%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-bromo-5-nitro-benzoic acid methyl ester (D11) (12.1 g, 46.5 mmol, 1 equiv) in MeOH (200 ml) was added SnCl2 (44 g, 233 mmol, 5 equiv). The resulting mixture was stirred at reflux for 4 h, cooled to room temperature and concentrated in vacuo. The residue was partitioned between ice-cold AcOEt and H2O. The aqueous phase was basified with 2N aqueous NaOH solution until a white precipitate appeared, then slowly with 12.5N aqueous NaOH solution until this precipitate disappeared. The temperature was kept below 10° C. during this addition. The two layers were separated and the aqueous phase extracted with AcOEt. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give 3-amino-5-bromo-benzoic acid methyl ester (D12) (9.9 g, 93%) as a brown solid.

후처리

  1. temperatureat reflux for 4 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ice-cold AcOEt and H2O
  4. additionThe temperature was kept below 10° C. during this addition
  5. customThe two layers were separated
  6. extractionthe aqueous phase extracted with AcOEt
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f8c6897872374bf189c3b3722ee2d2c3
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

연결된 노트

불러오는 중…