Water → 7-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran

HRID 1734207Notes

Reaction equation

HRID 1734207 reaction equation
[NH2:1][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.O>CN(C)C=O>[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([Br:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine

Product 1

HCID 537220087-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuranYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 10.0 grams (0.061 mole) of 7-amino-2,3-dihydro-2,2-dimethylbenzofuran in 150 mL of N,N-dimethylformamide is cooled in an ice-water bath, and a solution of 10.9 grams (0.061 mole) of N-bromosuccinimide in 50 mL of N,N-dimethylformamide is added in one portion. Upon completion of addition, the reaction mixture is maintained in the ice-water bath for about one hour. After this time the reaction mixture is poured into about 600 mL of water. The mixture is then extracted with two 200 mL portions of diethyl ether. The combined extracts are washed with two 100 mL portions of an aqueous 10% lithium chloride solution. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 12.3 grams of 7-amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum is consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionThe mixture is then extracted with two 200 mL portions of diethyl ether
  3. washThe combined extracts are washed with two 100 mL portions of an aqueous 10% lithium chloride solution
  4. dry with materialThe organic layer is dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe5ffaf1e9b24b2691107f6b79ad0bb4
Source dataset
uspto-grants-1996_07
Patent number
US05532370

Reaction notes

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