3-Bromophenol → HCID 69048156, compound

HRID 2383498Notes

Reaction equation

HRID 2383498 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[C:11]([O:15][C:16](=[O:29])[N:17]([C:19]1[CH:24]=[C:23](Cl)[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[CH3:18])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16](=[O:29])[N:17]([C:19]1[CH:24]=[C:23]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Br:3])[CH:5]=2)[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[CH3:18])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 115633-BromophenolHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 69048156HCID 69048156, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 50 ml of anhydrous N,N-dimethylformamide suspension containing 2.5 g of sodium hydride (55% weight) was added 10.0 g of 3-bromophenol, and the mixture was stirred under ice-cooling for 15 minutes. Subsequently, a solution of 16.6 g of N-(5-chloro-2-nitrophenyl)-N-methylcarbamic acid t-butyl ester dissolved in 70 ml of anhydrous N,N-dimethylformamide was added to the mixture in drops, and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was concentrated, followed by addition of water, neutralization using 3N hydrochloric acid and extraction with ethyl acetate. The extraction solution was washed with saturated saline, and then dried over anhydrous sodium sulfate. Ethyl acetate was distilled off from the extraction solution, and the insoluble product which deposited was washed with hexane and filtered, followed by drying under reduced pressure, to give the title compound (20.2 g, 83% yield).

Workup

  1. temperaturecooling for 15 minutes
  2. additionwas added to the mixture in drops
  3. stirringthe mixture was stirred at 100° C. for 3 hours
  4. concentrationThe reaction mixture was concentrated
  5. additionfollowed by addition of water, neutralization
  6. extraction3N hydrochloric acid and extraction with ethyl acetate
  7. washThe extraction solution was washed with saturated saline
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationEthyl acetate was distilled off from the extraction solution
  10. washthe insoluble product which deposited was washed with hexane
  11. filtrationfiltered
  12. customby drying under reduced pressure

Sources & evidence

ORD record
ord-23daaff052b4497cb62cb6460f890776
Source dataset
uspto-grants-2012_09
Patent number
US08263631B2

Reaction notes

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