Dimethylformamide → 2-(2-bromophenoxy)ethanol

HRID 2421352Notes

Reaction equation

HRID 2421352 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].CN(C)C=O.Br[CH2:21][CH2:22][OH:23]>O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:21][CH2:22][OH:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72442-BromophenolHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 111068022-(2-bromophenoxy)ethanolYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (23.8 g) and 2-bromophenol (14.9 g) were mixed with dimethylformamide (150 ml). 2-Bromoethanol (12.9 g) was added and the mixture heated to 50° C. for 18 h. The mixture was cooled and added to water (1500 ml). The product was extracted into diethyl ether (×3) and washed twice with dilute sodium hydroxide solution Evaporation gave 2-(2-bromophenoxy)ethanol (17.4 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe product was extracted into diethyl ether (×3)
  3. washwashed twice with dilute sodium hydroxide solution Evaporation

Sources & evidence

ORD record
ord-ebc7e4cb8b2648b29dd9f5e71a62f72a
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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