N-bromobutanimide → 5-Benzofuranacetic acid

HRID 1443828Notes

Reaction equation

HRID 1443828 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]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

To the solution of (2,3-dihydro-benzofuran-5-yl)-acetic acid (0.89 g, 5 mmol) and N-bromosuccinimide (0.89 g, 5 mmol) in carbon tetrachloride (10 mL) was added 10 mg of benzoyl peroxide. The mixture was refluxed for 3 h and cooled with ice. The solid was removed by filtration, the filtrate was concentrated, the residue was crystallized from 1:1 ethyl acetate:hexane to give a white solid (390 mg, 44%). 1H NMR (400 MHz, CDCl3) δ 10.5 (b s, 1H), 7.62 (d, J=2.2 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.21 (dd, J=8.4, 1.8 Hz, 1H), 6.74 (d, J=2.2 Hz, 1H), 3.75 (s, 2H).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. temperaturecooled with ice
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customthe residue was crystallized from 1:1 ethyl acetate

Sources & evidence

ORD record
ord-1aae98ab3724402e9bec668666ae16f1
Source dataset
uspto-grants-2010_02
Patent number
US07662824B2

Reaction notes

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