N-bromobutanimide → HCID 19029812, compound

HRID 2256375Notes

Reaction equation

HRID 2256375 reaction equation
[CH:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[C:5]=1[OH:16])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:17][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[C:5]([OH:16])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 111174551-Naphthalenol, 6-methoxy-2-(1-methylethyl)-

Product 1

HCID 19029812HCID 19029812, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

In 100 ml of DMF was dissolved 5 g of 2-isopropyl-6-methoxy-1-naphthol, and a solution of 4.03 g of N-bromosuccinimide in DMF (50 ml) was added under ice-cooling. The mixture was stirred under ice-cooling for 3 hours. The reaction mixture was then diluted with water and extracted with ethyl acetate and the organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent:diethyl ether:n-hexane:chloroform=10:50:1) to provide 6.1 g of 4-bromo-2-isopropyl-6-methoxy-1-naphthol. m.p. 81.5°-83.5° C.

Workup

  1. temperaturecooling
  2. temperaturecooling for 3 hours
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatography (eluent:diethyl ether:n-hexane:chloroform=10:50:1)

Sources & evidence

ORD record
ord-f83aca9838294af0b4c468a9f27bc92d
Source dataset
uspto-grants-1997_08
Patent number
US05654343

Reaction notes

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