Diethyl Ether → 5-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran

HRID 431783

반응식

HRID 431783 반응식
[CH3:1][C:2]1([CH3:11])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1.[Br:12]N1C(=O)CCC1=O.CCOCC>ClC(Cl)C>[Br:12][C:9]1[CH:8]=[CH:7][C:5]2[O:6][C:2]([CH3:11])([CH3:1])[CH2:3][C:4]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 806402,3-Dihydro-2,2-dimethylbenzofuran

생성물 1

HCID 2194755-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran수율 79%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

2,2-Dimethyl-2,3-dihydrobenzo[b]furan (prepared according to the method of Baker and Shulgin, J. Org. Chem., 28, 1963, 2468) (500 mg, 3.38 mmol) was taken up in dichloroethane (5.5 ml) and stirred at room temperature under nitrogen, and N-bromosuccinimide (661 mg, 3.72 mmol) added in one portion. The reaction was then refluxed for 2 h, ether was added (10 ml) and a white precipitate of succinimide filtered off. The filtrate was evaporated to dryness, and then purified by column chromatography using 5% ether in pentane as eluant to give the title product (604 mg, 79%); 1HNMR (400 MHz, CDCl3) δ: 1.43 (s, 6H), 2.92 (s, 2H), 6.54 (d, 1H), 7.16 (d, 1H), 7.19 (s, 1H); LRMS: M+H, 227. (TS+).

후처리

  1. temperatureThe reaction was then refluxed for 2 h
  2. filtrationa white precipitate of succinimide filtered off
  3. customThe filtrate was evaporated to dryness
  4. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-8cca403ca0b94291abad41bee111fcb1
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660756B2

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