Carbon tetrabromide → 5-(2,2-Dibromoethenyl)-3,3-dimethyl-2,3-dihydro-1-benzofuran

HRID 1888760Notes

Reaction equation

HRID 1888760 reaction equation
[CH3:1][C:2]1([CH3:13])[C:6]2[CH:7]=[C:8]([CH:11]=O)[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33](Br)(Br)([Br:35])[Br:34]>C1COCC1>[Br:34][C:33]([Br:35])=[CH:11][C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH2:3][C:2]([CH3:13])([CH3:1])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 205361803,3-Dimethyl-2,3-dihydrobenzofuran-5-carbaldehyde

Product 1

HCID 580472185-(2,2-Dibromoethenyl)-3,3-dimethyl-2,3-dihydro-1-benzofuranYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-dimethyl-2,3-dihydro-1-benzofuran-5-carbaldehyde (4.18 g, 23.7 mmol) and triphenylphosphine (15.5 g, 59.3 mmol) in THF (40 mL) was added carbon tetrabromide, and the mixture was stirred at room temperature for 15 min. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=49:1 to 7:3) to give the title compound (5.75 g, yield 73%) as an oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=49:1 to 7:3)

Sources & evidence

ORD record
ord-838cfe5b2e9642da89670dd0f827f360
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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