Ethanol → Ethyl 2-bromo-4-fluorobenzoate

HRID 8584Notes

Reaction equation

HRID 8584 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[Br:7][C:8]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].C(N(CC)CC)C.C(O)C>C1(C)C=CC=CC=1.C(Cl)Cl.O>[Br:7][C:8]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:9]=1[C:10]([O:5][CH2:1][CH3:2])=[O:11]

Participants

8

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 12681692-Bromo-4-fluorobenzoic acid

Product 1

HCID 21983528Ethyl 2-bromo-4-fluorobenzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

281 mg (2.21 mmol) of oxalyl chloride are added to a solution of 220 mg (1.01 mmol) of 2-bromo-4-fluorobenzoic acid in 5 ml of absolute toluene under argon, and the mixture is stirred at RT for 4 hours. The solvent is removed in vacuo, and the residue is taken up three times in DCM and the solvent is removed each time in vacuo. A yellow oil is obtained and is dissolved in a little DCM. 213 mg (2.10 mmol) of triethylamine and 2 ml of ethanol are added to the solution, and the mixture is stirred at RT for three hours. The reaction mixture is diluted with twice the volume of distilled water and extracted with DCM. The solvent of the organic phase is removed in vacuo, and the residue is chromatographed on silica gel (eluent: DCM/methanol 20:1). 100 mg (39% of theory) of the product are obtained.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe solvent is removed each time in vacuo
  3. customA yellow oil is obtained
  4. stirringthe mixture is stirred at RT for three hours
  5. extractionextracted with DCM
  6. customThe solvent of the organic phase is removed in vacuo
  7. customthe residue is chromatographed on silica gel (eluent: DCM/methanol 20:1)
  8. custom100 mg (39% of theory) of the product are obtained

Sources & evidence

ORD record
ord-e2abdf35125f4a8789256a10ba8b5587
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

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