3,5-Bis(bromomethyl)benzoic acid ethyl ester → 3-Bromomethyl-5-{ethoxymethyl}benzoic acid, ethyl ester

HRID 1531921Notes

Reaction equation

HRID 1531921 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH2:11][Br:12])[CH:8]=[C:7]([CH2:13]Br)[CH:6]=1)[CH3:2].[O-:16][CH2:17][CH3:18].[K+]>C(O)C>[Br:12][CH2:11][C:9]1[CH:10]=[C:5]([CH:6]=[C:7]([CH2:13][O:16][CH2:17][CH3:18])[CH:8]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

4

Reactant 2

HCID 154403433,5-Bis(bromomethyl)benzoic acid ethyl esterHCID 23670592Potassium ethoxide

Product 1

HCID 1317224293-Bromomethyl-5-{ethoxymethyl}benzoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 3,5-bis[bromomethyl]benzoic acid ethyl ester (3g) in ethanol (100 ml) was treated with potassium ethoxide (0.75 g) and stirred overnight. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated and the residue purified by chromatography eluting with 10% ethyl acetate in isohexane. Yield 1.3 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customthe residue purified by chromatography
  5. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-9466452d05ac4296b29514a64a1baec8
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

Loading…