Pyridiniumtribromide → 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

HRID 1509745노트

반응식

HRID 1509745 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[CH:15]=[C:14]4[CH2:17][CH2:18][CH2:19][C:20](=[O:21])[C:13]4=[CH:12][C:11]=3[O:10][CH2:9][C:8]=2[CH:22]=1)(=[O:3])[CH3:2].C(Cl)Cl.CO.[Br-:28].[Br-:29].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CCOC(C)=O>[Br:28][CH:19]1[CH2:18][CH2:17][C:14]2=[CH:15][C:16]3[C:7]4[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH2:2][Br:29])=[CH:22][C:8]=4[CH2:9][O:10][C:11]=3[CH:12]=[C:13]2[C:20]1=[O:21]

참가 물질

5

반응물 3

HCID 21124087PyridiniumtribromideHCID 21226129Dichloromethane methanolHCID 866883753-acetyl-10,11-dihydro-5H-dibenzo(c,g)chromen-8(9H)-one

생성물 1

HCID 866883729-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
35 °C

실험 절차

A 20 mL vial with a stir bar was charged with 3-acetyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (100 mg, 0.366 mmol), 9:1 CH2Cl2/MeOH (3.4 mL) and pyridinium tribromide (246 mg, 0.769 mmol). The solution was heated to 35° C. After 30 minutes, the reaction was judged complete. The mixture was cooled to ambient temperature, diluted with EtOAc (50 mL) and sequentially washed with saturated aqueous Na2S2O3 (20 mL), 2% aqueous NaHCO3 (20 mL), water (20 mL), and brine (10 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure resulting in 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (68 mg, 41%): 400 MHz 1H NMR (CDCl3) δ 8.03-8.01 (m, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.82 (s, 1H), 7.71 (s, 1H), 7.67 (s, 1H), 5.19 (s, 2H), 4.74 (dd, J=4.1, 4.1 Hz, 1H), 4.45 (s, 2H), 3.37-3.29 (m, 1H), 2.99-2.92 (m, 1H), 2.59-2.46 (m, 2H).

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. washsequentially washed with saturated aqueous Na2S2O3 (20 mL), 2% aqueous NaHCO3 (20 mL), water (20 mL), and brine (10 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customresulting in 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (68 mg, 41%)

출처 및 근거

ORD 기록
ord-cff16c0c59b949d285590f08438753b7
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221833B2

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