N-bromobutanimide → 3,7-Dibromo-2,3-dihydro-2,2-dimethylbenzofuran

HRID 1734166

Reaction equation

HRID 1734166 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[C:10]=2[O:9][C:8]1([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2720047-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran

Product 1

HCID 190407783,7-Dibromo-2,3-dihydro-2,2-dimethylbenzofuran

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirring mixture of 7.0 grams (0.031 mole) of 7-bromo-2,3-dihydro-2,2-dimethylbenzofuran and 5.5 grams (0.031 mole) of N-bromosuccinimide in 150 mL of carbon tetrachloride is heated to reflux while irradiating with a sun lamp. The refluxing reaction mixture is stirred for about three hours, then it is cooled to ambient temperature. After this time the reaction mixture is washed with two 50 mL portions of aqueous 5% sodium bicarbonate solution, and one 50 mL portion of water. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 3,7-dibromo-2,3-dihydro-2,2-dimethylbenzofuran.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. customwhile irradiating with a sun lamp
  4. customThe refluxing reaction mixture
  5. washAfter this time the reaction mixture is washed with two 50 mL portions of aqueous 5% sodium bicarbonate solution, and one 50 mL portion of water
  6. dry with materialThe organic layer is dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b7c0329051c491c9058a87f2aa8ea35
Source dataset
uspto-grants-1996_07
Patent number
US05532367

Linked notes

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