2-Methoxyethanol → 3-Bromomethyl-5-[2-methoxyethoxymethyl]benzoic acid ethyl ester

HRID 1531918Notes

Reaction equation

HRID 1531918 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH2:13][Br:14])[CH:10]=[C:9]([CH2:15]Br)[CH:8]=1)[CH3:4].[CH3:18][O:19][CH2:20][CH2:21][OH:22]>>[CH2:3]([O:5][C:6](=[O:17])[C:7]1[CH:8]=[C:9]([CH2:15][O:22][CH2:21][CH2:20][O:19][CH3:18])[CH:10]=[C:11]([CH2:13][Br:14])[CH:12]=1)[CH3:4]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 154403433,5-Bis(bromomethyl)benzoic acid ethyl ester

Product 1

HCID 702251523-Bromomethyl-5-[2-methoxyethoxymethyl]benzoic acid ethyl ester

Procedure

Sodium hydride (0.357 g, 60% dispersion in oil) was added to 2methoxyethanol (10 ml) with stirring. After 10 minutes 3,5-bis[bromomethyl]benzoic acid ethyl ester (J. Chem. Soc. Chem. Commun. 1992, 22, 1647) (3 g) was added and the mixture stirred for 3 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. Purified by chromatography eluting with 20% ethyl acetate in isohexane. Yield 0.45 g.

Workup

  1. stirringthe mixture stirred for 3 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customPurified by chromatography
  6. washeluting with 20% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-77d6f5ba0a0c41c184264e70d51ce06e
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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