Ethyl bromoacetate → Ethyl 2-[2-cyano-5-(phenylmethoxy)phenoxy]acetate

HRID 1740489Notes

Reaction equation

HRID 1740489 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>O1CCCC1.CN(C)C=O>[C:6]([C:5]1[CH:8]=[CH:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:4]=1[O:3][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])#[N:7]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 154532344-(Benzyloxy)-2-hydroxybenzonitrile

Product 1

HCID 54227701Ethyl 2-[2-cyano-5-(phenylmethoxy)phenoxy]acetateYield 80.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

9.7 g (0.20 mol) of 50% sodium hydride are slowly added portionwise to a solution of 46 g (0.20 mol) of 2-hydroxy-4-(phenylmethoxy)benzonitrile in a mixture of 450 ml of tetrahydrofuran and 450 ml of dimethylformamide. The mixture is stirred for 30 minutes and then 22.4 ml (0.20 mol) of ethyl bromoacetate are added dropwise. Reaction is allowed to take place for 30 minutes, the reaction mixture is then poured into ice-cold water and the product is extracted with ethyl acetate. The organic phase is then washed with water, dried over sodium sulphate and concentrated under reduced pressure. After trituration of the residue in diisopropyl ether, 50 g of product are obtained.

Workup

  1. customReaction
  2. customfor 30 minutes
  3. additionthe reaction mixture is then poured into ice-cold water
  4. extractionthe product is extracted with ethyl acetate
  5. washThe organic phase is then washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1468c7259434ad9be2f00bf21a1c8c2
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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