Ethyl bromoacetate → HCID 22321977, compound

HRID 496647Notes

Reaction equation

HRID 496647 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([Cl:12])[C:3]=1[CH:4]=[O:5].[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([CH:7]=[C:6]([Cl:12])[C:3]=1[CH:4]=[O:5])[CH2:10][O:11][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 102420322,6-Dichloro-4-hydroxymethylbenzaldehyde

Product 1

HCID 22321977HCID 22321977, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 500 mg (2.4 mmol) A3 in 5 ml dry dimethyl formamide under nitrogen was cooled in an ice bath and 73 mg (3.0 mmol) sodium hydride was added and the mixture was stirred for 10 minutes. After addition of 410 mg (2.6 mmol) ethyl bromoacetate, the mixture was heated to 110° C. for 8 h. The solvent was removed in vacuo and the residue was taken up in ethyl acetate and washed with water. The organic layer was dried over sodium sulphate and evaporated to dryness. Purification of the residue by column chromatography on SiGel (heptane/ethyl acetate 4:1) yielded 40 mg (6%) A15.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated to dryness
  5. customPurification of the residue by column chromatography on SiGel (heptane/ethyl acetate 4:1)
  6. customyielded 40 mg (6%) A15

Sources & evidence

ORD record
ord-c593ac71b2fd41a4b020f49d2f1a41c9
Source dataset
uspto-grants-2005_09
Patent number
US06946471B2

Reaction notes

Loading…