Water → HCID 21914366, compound

HRID 2421341Notes

Reaction equation

HRID 2421341 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1O.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:15]([O:4][CH:1]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[Br:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72442-BromophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 21914366HCID 21914366, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (9.12 g) was suspended in dimethylformamide (25 ml) and 2-bromophenol (3.46 g) was added portionwise. Benzyl bromide (3.76 g) was added and the mixture heated to 60° C. for 4 h. After cooling the mixture was added to water (250 ml) and extracted three times with diethyl ether. The organic layer was separated and washed with 2M sodium hydroxide solution (100 ml) before drying over sodium sulphate. After filtration, evaporation yielded (5.13 g) as a colourless oil.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted three times with diethyl ether
  3. customThe organic layer was separated
  4. washwashed with 2M sodium hydroxide solution (100 ml)
  5. dry with materialbefore drying over sodium sulphate
  6. filtrationAfter filtration, evaporation
  7. customyielded (5.13 g) as a colourless oil

Sources & evidence

ORD record
ord-f791c83522e044808bd2a96ee5ca5605
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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