N-bromobutanimide → 5-Benzofuranacetic acid

HRID 1661802Notes

Reaction equation

HRID 1661802 reaction equation
BrN1C(=O)CCC1=O.[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH2:18][C:19]([OH:21])=[O:20])=[CH:17][C:12]=2[CH2:11][CH2:10]1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH2:18][C:19]([OH:21])=[O:20])=[CH:17][C:12]=2[CH:11]=[CH:10]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27374552,3-Dihydro-5-benzofuranacetic acid

Product 1

HCID 234388925-Benzofuranacetic acidYield 44.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (0.89 g, 5.0 mmol) was added to a solution of 2,3-dihydrobenzofuran-5-ylacetic acid (0.89 g, 5.0 mmol) and benzoyl peroxide (10 mg) in carbon tetrachloride (100 mL) and refluxed for 3 hours. The mixture was cooled to room temperature, filtered and concentrated. The product was recrystallized from ethyl acetate:hexane (2:1) to give a 0.39 g (44%) of white solid. 1H NMR (CD3OD) δ 7.62 (1H, d, J=2.4 Hz), 7.52 (1H, d, J=0.8 Hz), 7.46 (1H, d, J=8.4 Hz), 7.21 (1H, dd, J=1.6, 8.4 Hz), 6.74 (1H, d, J=3.2 Hz), 3.74 (2H, s).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe product was recrystallized from ethyl acetate:hexane (2:1)

Sources & evidence

ORD record
ord-48f5bf3a53634a7ab3da124c25086a1f
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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