Hydroquinone → 2-Bromo-1,4-benzenediol

HRID 1914781

반응식

HRID 1914781 반응식
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Br:9]Br.C(Cl)(Cl)Cl.CO>C(OC)(C)(C)C>[Br:9][C:7]1[CH:8]=[C:1]([OH:2])[CH:3]=[CH:4][C:5]=1[OH:6]

참가 물질

5

반응물 3

HCID 785HydroquinoneHCID 24408BromineHCID 21584188Chloroform methanol

생성물 1

HCID 685022-Bromo-1,4-benzenediol

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
0 °C

실험 절차

To a solution of hydroquinone Q-1 (10 g, 90.90 mmol) in MTBE (methyl tert-butyl ether) (100 mL) at −5° C. was added bromine (17.4 g, 90.90 mmol). The reaction mixture was stirred at 0° C. for 30 min. Solvent was removed in vacuo and the crude product was purified by column chromatography (SiO2, 2% MeOH—CHCl3) to afford compound Q-2 (13 g, 75%) as a solid. TLC Rf=0.6 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 6.94 (app d, 1H), 6.88 (d, J=8.7 Hz, 1H), 6.72 (dd, J=8.7, 2.8 Hz, 1H), 5.19 (s, 2H) (Synlett 2000, 11, 1561-1564).

후처리

  1. customSolvent was removed in vacuo
  2. customthe crude product was purified by column chromatography (SiO2, 2% MeOH—CHCl3)
  3. customto afford compound Q-2 (13 g, 75%) as a solid

출처 및 근거

ORD 기록
ord-0ccd451e670042eaa2c5e5a153cc8d9f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614237B2

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