Bromoacetate → HCID 131727725, compound

HRID 1433043Notes

Reaction equation

HRID 1433043 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([OH:10])[CH:3]=1.[C:11](=[O:14])([O-])[O-:12].[K+].[K+].Br[CH2:18][C:19]([O-])=O.[CH3:22]N(C=O)C>O>[CH2:18]([O:12][C:11](=[O:14])[CH2:22][O:10][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])[CH3:19]

Participants

6

Reactant 4

HCID 6226BromoacetateHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 131727725HCID 131727725, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-chloro-2-hydroxy-benzylalcohol (9.7 g, 61.3 mmol) in 100 ml of DMF is added potassium carbonate (17 g, 123.1 mmol), and the resulting suspension is stirred for 15 minutes at room temperature. Ethyle bromoacetate (7.96 ml, 67 mmol) is added and the mixture is stirred at room temperature for two days. The mixture is poured in 500 ml of water, extracted with ethyl acetate (500 ml). The ethyl acetate layer is separated, washed with water (500 ml), brine (500 ml) and dried over magnesium sulfate. After concentration ethyl-(2-hydroxymethyl-5-chloro-phenoxy)-acetate is obtained as a white solid (13.7 g, 91% yield) C11H13ClO4, MS (M+) m/z: 244, 246, Cl pattern.

Workup

  1. stirringthe mixture is stirred at room temperature for two days
  2. extractionextracted with ethyl acetate (500 ml)
  3. customThe ethyl acetate layer is separated
  4. washwashed with water (500 ml), brine (500 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration ethyl-(2-hydroxymethyl-5-chloro-phenoxy)-acetate

Sources & evidence

ORD record
ord-7667cedd26194ee68b41a2e227a8bbfa
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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