2-Ethyl-1-butanol → 4-Bromomethyl-benzoic acid 2-ethyl-butyl ester

HRID 1591983Notes

Reaction equation

HRID 1591983 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH2:12]([CH:14]([CH2:17][CH3:18])[CH2:15][OH:16])[CH3:13]>C(Cl)Cl>[CH2:12]([CH:14]([CH2:17][CH3:18])[CH2:15][O:16][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[CH:4][CH:5]=1)[CH3:13]

Participants

4

Reactant 2

HCID 73582-Ethyl-1-butanolHCID 50682894-Bromomethyl-benzoyl chloride

Product 1

HCID 671383384-Bromomethyl-benzoic acid 2-ethyl-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the title A compound, 4-bromomethyl-benzoyl chloride (466 mg, 2 mmol) in 3 mL of CH2Cl2 is added dropwise to a solution of 2-ethyl-1-butanol (204 mg, 2 mmol) and TEA (202 mg, 2 mmol) in 10 mL of CH2Cl2 at 0˜5° C. over 30 min. The reaction is allowed to warm to RT and stirred overnight. The solvent is evaporated and the residue is partitioned between hexane and water. The organic phase is dried over anhydrous MgSO4 and concentrated. The residue is chromatographic on silica gel using EtOAc/hexane (gradient 90-70) to give 4-bromomethyl-benzoic acid 2-ethyl-butyl ester as a colorless oil.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between hexane and water
  3. dry with materialThe organic phase is dried over anhydrous MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e165bb54b2b742f79303a7e3dbe9fbff
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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