Dimethylcyanamide → 5-Bromophthalide

HRID 1017787Notes

Reaction equation

HRID 1017787 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.BrN1C(=O)CCC1=O.C(#N)N(C)C>C(OC)(=O)CC.[Hg]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][CH:10]=1)[C:6](=[O:8])[O:7][CH2:11]2

Participants

6

Reactant 3

HCID 15112DimethylcyanamideHCID 67184N-bromobutanimideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 6031445-Bromophthalide

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 11124Methyl propionateSolvent

Procedure

A solution of 0.43 g (2.0 mmol) of 4-bromo-2-methyl-benzoic acid, 0.34 g (1.9 mmol) of N-bromosuccinimide and 20 mg of azaisobutyronitrile in 7 ml of methyl propionate is heated to boiling for 1 hour under a nitrogen atmosphere and irradiated with a mercury vapour lamp. The reaction mixture is concentrated, taken up in methylene chloride, washed with H2O, dried with Na2SO4 and purified by flash chromatography (silica gel; ethyl acetate/petroleum ether=5:95 to 15:85).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washwashed with H2O
  3. dry with materialdried with Na2SO4
  4. custompurified by flash chromatography (silica gel; ethyl acetate/petroleum ether=5:95 to 15:85)

Sources & evidence

ORD record
ord-a10304388c814a7f8333f061b1e05efe
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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