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

HRID 22924

反応式

HRID 22924 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-4aa208ddefc74a5a9b1404a45bd9e745
出典データセット
uspto-grants-2005_02
特許番号
US06849649B2

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