N-bromobutanimide → 5-Bromo-2-ethyl-2,3-dihydro-benzofuran

HRID 1866539Notes

Reaction equation

HRID 1866539 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([CH:11]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12]1)[CH3:10]>ClCCl>[Br:1][C:17]1[CH:18]=[CH:19][C:13]2[O:12][CH:11]([CH2:9][CH3:10])[CH2:15][C:14]=2[CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12231169ethyl-dihydrobenzofuran

Product 1

HCID 579782475-Bromo-2-ethyl-2,3-dihydro-benzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Bromosuccinimide (8.66 g, 48.6 mmol) was added to a solution of 2-ethyl-2,3-dihydrobenzofuran (preparation 98) in dichloromethane (70 mL) and the mixture was stirred at room temperature for 18 hours. The mixture was then diluted with dichloromethane (200 mL) and washed with water (200 mL) and sodium meta-bisulphite (200 mL). The organic solution was dried over magnesium sulfate and concentrated in vacuo to give a yellow oil that was purified by HPLC using a Chiralcel OJ 250*20 mm column and hexane:isopropanol (95:5) as the eluant to afford the first enantiomer of the title compound. Further elution provided the second isomer of the title compound, 2.95 g. 1H NMR (400 MHz, CDCl3) δ: 7.24 (1H, m), 7.18 (1H, m), 6.62 (1H, d), 4.75 (1H, m), 3.30-3.20 (1H, m), 2.92-2.80 (1H, m), 1.77-1.88 (1H, m), 1.75-1.65 (1H, m) 1.00 (3H, m) ppm.

Workup

  1. washwashed with water (200 mL) and sodium meta-bisulphite (200 mL)
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a yellow oil that
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-59bc7c80ca9b4f53a31d77e1114ad350
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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