Hexane → 5-Bromo-6-methyl-1-benzofuran

HRID 1856682Notes

Reaction equation

HRID 1856682 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][CH2:10][CH2:11][CH2:12][CH2:13]C.[C:15]([O:18][CH2:19][CH3:20])(=O)[CH3:16].CCCCCC>ClC(Cl)C>[Br:1][C:11]1[C:12]([CH3:13])=[CH:16][C:15]2[O:18][CH:19]=[CH:20][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 21226206Ethyl acetate hexane

Product 1

HCID 180015115-Bromo-6-methyl-1-benzofuranYield 22%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Part E. A solution of the above compound (780 mg) and N-bromosuccinimide (1.24 g, 6.97 mol) in dichloroethane (10 mL) was heated to reflux overnight, then cooled, filtered and evaporated. Column chromatography (hexane, then 2:98 ethyl acetate-hexane) gave first 5-bromo-6-methylbenzofuran (270 mg, 1.27 mmol, 22%), then 5-bromo-6-methyl-2,3-dihydrobenzofuran (923 mg, 4.33 mol, 75%), both as solids. For the dihydro product: TLC RF 0.35 (2:98 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3): d 7.31 (1H, s), 6.68 (1H, s), 4.56 (2H, t, J=8.8 Hz), 3.17 (2H, t, J=8.8 Hz), 2.33 (3H, s). MS(H2O-GC/MS): m/e 215 (76), 213 (100).

Workup

  1. temperatureto reflux overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-71f360cd9b434909beb0cf9377035304
Source dataset
uspto-grants-2000_11
Patent number
US06143743

Reaction notes

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