Bromine → 5-Bromo-3,3-diethyl-1,3-dihydro-2H-indol-2-one

HRID 277000노트

반응식

HRID 277000 반응식
[CH2:1]([C:3]1([CH2:13][CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])[CH3:2].C([O-])(=O)C.[Na+].[Br:20]Br>C(O)(=O)C.O>[Br:20][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:12])[C:3]2([CH2:1][CH3:2])[CH2:13][CH3:14]

참가 물질

6

반응물 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 151532213,3-diethyl-2,3-dihydro-1H-indol-2-one

생성물 1

HCID 219862505-Bromo-3,3-diethyl-1,3-dihydro-2H-indol-2-one

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

A solution of 3,3-diethylindol-2-one (8 g, 40 mmol) and sodium acetate (4 g, 48 mmol) in acetic acid (100 ml) was treated with bromine (6.4 g, 40 mmol). After 30 min. the mixture was diluted with water and extracted with EtOAc (2×); the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, then brine, dried (MgSO4) and evaporated to afford the crude product (7.6 g, 75%). A sample was recrystallized from EtOAc/hexane to obtain 5-bromo-1,3-dihydro-3,3-diethyl-[2H]-indol-2-one, m. p. 164-165° C.; 1H-NMR (DMSO-d6) δ 10.45 (s, 1H), 7.41-7.40(d, 1H, J=2.2 Hz), 7.34-7.31 (m, 1H), 6.78-6.76 (d, 1H, J=8.2 Hz), 1.78-1.65 (m, 4H), 0.50-0.46 (m, 6H); MS (-ESI) m/z 266/268 (M−H).

후처리

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution
  3. dry with materialbrine, dried (MgSO4)
  4. customevaporated
  5. customto afford the crude product (7.6 g, 75%)
  6. customA sample was recrystallized from EtOAc/hexane

출처 및 근거

ORD 기록
ord-ed1ba6631a054e9c8ebf9aa588c7baa7
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355648B1

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