Water → 5-Bromo-2-oxindole

HRID 6979

반응식

HRID 6979 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C([O-])(=O)C.[Na+].[Br:16]Br.O>C(Cl)(Cl)Cl.CCOC(C)=O>[Br:16][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2

참가 물질

7

반응물 4

HCID 962WaterHCID 24408BromineHCID 321710OxindoleHCID 517045Sodium Acetate

생성물 1

HCID 6111935-Bromo-2-oxindole수율 97.3%

시약·촉매·용매 2

HCID 6212Chloroform용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (×2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96%) as an off-white solid which was used without further purification: m.p. 221–223° C.; 1H NMR (DMSO-d6) δ 3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) δ 36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

후처리

  1. extractionThe aqueous layer was extracted with EtOAc (×2)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-fbb70cf1aa6d4f91b0623384d82a6ec4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084168B2

연결된 노트

불러오는 중…