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

HRID 22924Notes

Reaction equation

HRID 22924 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-4aa208ddefc74a5a9b1404a45bd9e745
Source dataset
uspto-grants-2005_02
Patent number
US06849649B2

Reaction notes

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