Dichloromethane → 4,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

HRID 1699746Notes

Reaction equation

HRID 1699746 reaction equation
[Br:1][C:2]1[C:10]([CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[C:3]=1[Br:16].ClCCl.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C=O.CO>[Br:16][C:3]1[C:4]2[O:8][CH2:7][CH2:6][C:5]=2[C:9]2[C:13](=[O:15])[CH2:12][CH2:11][C:10]=2[C:2]=1[Br:1]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 110245373-(6,7-dibromo-2,3-dihydrobenzofuran-5-yl)propanoic Acid

Product 1

HCID 117272814,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-oneYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(6,7-dibromo-2,3-dihydrobenzofuran-5-yl)propionic acid (10.0 g, 28.6 mmols), dichloromethane (35 mL), thionyl chloride (5.11 g, 40.8 mmols) and N,N-dimethylformamide (30 mg) was heated to reflux for 1 hour. After cooling, aluminum chloride (4.66 g, 43.3 mmols) was added to the reaction mixture a trot more than 0° C. and then the mixture was stirred for 30 min. The reaction mixture was poured into precooled methanol (200 mL), then stirred for 30 min. Crystals precipitated were collected by filtration, washed with water (500 mL) followed by methanol (500 mL) to obtain 7.9 g (yield: 89%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. stirringstirred for 30 min
  5. customCrystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with water (500 mL)

Sources & evidence

ORD record
ord-48d5da54d39348e8b7e85b4cdf353cf7
Source dataset
uspto-grants-2002_02
Patent number
US06348485B1

Reaction notes

Loading…