1-Chloroethyl 5-(2,4-difluorophenyl)salicylate → 1-(Ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate

HRID 1719730Notes

Reaction equation

HRID 1719730 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:20]=[C:13]([C:14]([O:16][CH:17](Cl)[CH3:18])=[O:15])[C:12]([OH:21])=[CH:11][CH:10]=1.[C:22](=[O:27])([O-:26])[O:23][CH2:24][CH3:25].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:20]=[C:13]([C:14]([O:16][CH:17]([O:27][C:22]([O:23][CH2:24][CH3:25])=[O:26])[CH3:18])=[O:15])[C:12]([OH:21])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 202667581-Chloroethyl 5-(2,4-difluorophenyl)salicylateHCID 23677505Sodium ethyl carbonate

Product 1

HCID 134913951-(Ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-chloroethyl 5-(2,4-difluorophenyl)salicylate (5.0 g) in about 40 ml of DMF is added portionwise 3.0 g of sodium ethyl carbonate. The reaction is stirred at room temperature and then concentrated in vacuo. The concentrate is partitioned between ether/ethyl acetate and acidified water. The organic layer is separated and the aqueous layer is again extracted with ether, the organic layers are pooled and washed with water followed by drying and concentration to the crude product. After further purification by chromatography as described in Example 1, the product is crystallized from hexane to afford pure 1-(ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe concentrate is partitioned between ether/ethyl acetate
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is again extracted with ether
  5. washwashed with water
  6. customby drying
  7. concentrationconcentration to the crude product
  8. customAfter further purification by chromatography
  9. customthe product is crystallized from hexane

Sources & evidence

ORD record
ord-2e181670a9584618adce48a18302962e
Source dataset
uspto-grants-1985_09
Patent number
US04542158

Reaction notes

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