Bromide ion → HCID 54336416, compound

HRID 1069083Notes

Reaction equation

HRID 1069083 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].Br[CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].[Br-]>CN(C)C=O>[C:25]([O:24][C:22]([NH:21][CH2:20][CH2:19][O:17][C:13]1[CH:12]=[C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=2)[CH:16]=[CH:15][CH:14]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 5097338Methyl 3-(3-hydroxyphenyl)benzoate

Product 1

HCID 54336416HCID 54336416, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3′-hydroxy-[1,1′-biphenyl]-3-carboxylic acid methyl ester (667 mg) and 2-bromo-1-[(tert-butoxycarbonyl)amino]ethane (980 mg) in N, N-dimethylformamide (15 mL) was treated with potassium carbonate (2.0 g). The mixture was stirred at room temperature for 30 min, and heated to 50° C. in an oil bath for 14 h. Additional bromide (396 mg) was added and the mixture was heated an additional 36 h. The mixture was cooled to room temperature and partitioned between 1:1 hexane ethyl acetate and water. The organic layer was separated, washed with water, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel chromatography (eluting with 5:1 hexane/ethyl acetate) afforded the title compound as a colorless oil (826 mg).

Workup

  1. temperatureheated to 50° C. in an oil bath for 14 h
  2. temperaturethe mixture was heated an additional 36 h
  3. temperatureThe mixture was cooled to room temperature
  4. custompartitioned between 1:1 hexane ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude product
  11. customPurification
  12. washby silica gel chromatography (eluting with 5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e87513f584e5401aa2510ce94adb9a59
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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