Iodine → 5-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran

HRID 2194555

반응식

HRID 2194555 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][C:10]([CH3:12])=[CH2:11])[CH:3]=1.II>C(Cl)Cl.C(OC)(C)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:10]([CH3:12])([CH3:11])[CH2:9][C:4]=2[CH:3]=1

참가 물질

5

반응물 2

HCID 807IodineHCID 86761724HCID 86761724, 화합물

생성물 1

HCID 2194755-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 15413tert-Butyl methyl ether용매

실험 절차

To a solution of 4-bromo-2-(2-methylallyl)phenol (7) (4.5 g, 19.8 mmol) in CH2Cl2 (250 mL) was added iodine (1.3 g, 4.95 mmol) and the mixture stirred at room temperature for 48 h. The mixture was then diluted with methyl tert-butyl ether (100 mL) and washed with H2O (50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, eluting with 5% ethyl acetate in hexanes) to give the title compound (8) (4.0 g, 88%) as yellow liquid. 1H NMR (CDCl3, 400 MHz) δ 7.24 (s, 1H), 7.20 (d, J=8.4 Hz, 1H), 6.61 (d, J=8.4 Hz, 1H), 3.00 (s, 2H), 1.47 (s, 6H); MS (ESI, M+H+) C10H12BrO, calcd. 227.1. found 227.0, 229.0.

후처리

  1. washwashed with H2O (50 mL), brine (50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (silica gel, eluting with 5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-2b90285366544913aa61d40ffbd08321
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334292B1

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