Acetopiperone → 1-(1,3-Dioxaindan-5-yl)-2-bromoethan-1-one

HRID 2298589Notes

Reaction equation

HRID 2298589 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1)=[O:3].C=CC1C=C[NH+]=CC=1.[Br-:21].[Br-].[Br-]>CO>[CH2:11]1[O:12][C:6]2[CH:5]=[C:4]([C:2]([CH2:1][Br:21])=[O:3])[CH:9]=[CH:8][C:7]=2[O:10]1

Participants

4

Reactant 2

HCID 76622AcetopiperoneHCID 18537368HCID 18537368, compound

Product 1

HCID 2437771-(1,3-Dioxaindan-5-yl)-2-bromoethan-1-oneYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.5 g (15.23 mmol) of 3,4-methylenedioxy acetophenone in 200 mL of anhydrous methanol was added 61 mmol (20 g) of poly(4-vinylpyridinium tribromide), Aldrich Chemical Co., and allowed to reflux for 2.5 h. The solution was filtered and concentrated. 1-(2H-benzo[3,4-d]1,3-dioxolen-5-yl)-2-bromoethan-1-one (1.4 g, 38% yield) was obtained methylene chloride/hexanes as off-white crystals. 1H-NMR (DMSO-d6; 300 MHz) δ 8.2 (s, 1H), 8.07 (s, 1H), 7.61-7.64 (m,2H), 7.01-7.04 (dd, J=1.2 Hz and 7.1 Hz, 1H), 6.09 (s, 2H), 3.86 (s, 3H), 2.75 (s, 3H).

Workup

  1. temperatureto reflux for 2.5 h
  2. filtrationThe solution was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7ecf8b9643594be2b7d10f3ac71fab1a
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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