Oxalyl chloride → HCID 15628583, compound

HRID 8398Notes

Reaction equation

HRID 8398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:11]=2[C:12](O)=[O:13])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[F:19][C:16]1[CH:17]=[CH:18][C:10]2[CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=3[C:12](=[O:13])[C:11]=2[CH:15]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 220157782-[2-(4-Fluorophenyl)ethyl]-5-fluorobenzoic Acid

Product 1

HCID 15628583HCID 15628583, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[2-(4-fluorophenyl)ethyl]-5-fluorobenzoic acid (2.02 g, 7.71 mmol, 1 equiv) and oxalyl chloride (1.37 g, 10.8 mmol, 1.4 equiv) in CH2Cl2 (20 mL) was refluxed for 30 min. The resulting solution was then added to a stirring suspension of aluminum chloride (1.44 g, 10.8 mmol, 1.4 equiv) in CH2Cl2 (50 mL). This mixture was refluxed for 1 h. The reaction mixture was then washed with 1N HCL (3×20 mL), aq. satd. NaCl (1×50 mL), and H2O (1×50 mL) The organic layer was dried (anhyd. Na2SO4) and rotary evaporated to provide 1.6 g of a light-orange-colored semisolid. This material was chromatographed (3:1 hexane/CHCl3) through silica gel (150 mm×25-mm dia.). Evaporation of the combined fractions containing product provided 0.93 g (49%) of the desired product as a light-yellow shiny solid.

Workup

  1. temperaturewas refluxed for 30 min
  2. temperatureThis mixture was refluxed for 1 h
  3. washThe reaction mixture was then washed with 1N HCL (3×20 mL), aq. satd
  4. dry with materialNaCl (1×50 mL), and H2O (1×50 mL) The organic layer was dried (anhyd. Na2SO4)
  5. customrotary evaporated

Sources & evidence

ORD record
ord-d715ecfdb67a41a48509fd54ef0d2331
Source dataset
uspto-grants-2006_08
Patent number
US07087765B2

Reaction notes

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