Oxalyl chloride → 3-Fluoro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

HRID 916236Notes

Reaction equation

HRID 916236 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:8][CH2:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 220158012-[2-(4-Fluorophenyl)ethyl]benzoic acid

Product 1

HCID 144059923-Fluoro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-oneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[2-(4-fluorophenyl)ethyl]benzoic acid (4.00 g, 16.4 mmol, 1 equiv) and oxalyl chloride (2.0 mL, 2.9 g, 23 mmol, 1.4 equiv) in CH2Cl2 (50 mL) was refluxed for 30 min. The resulting solution was then added to a stirring suspension of aluminum chloride (3.0 g, 2.2 mmol, 1.4 equiv) in CH2Cl2 (50 mL). This mixture was refluxed for 1 h. The reaction mixture was then washed with 1N HCl (3×50 mL), aq. satd. NaCl (1×50 mL), and H2O (1×50 mL). The organic layer was dried (anh. Na2SO4) and rotary evaporated (75° C.) to provide 3.7 g of a dark-brown oil. This oil was flash chromatographed (20:1 hexane/EtOAc) through flash silica gel (250 mm×25 mm). Evaporation of the combined fractions of interest provided 1.58 g (42.6%) of the desired product as a yellow oil.

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 (3×50 mL), aq. satd
  4. dry with materialThe organic layer was dried (anh. Na2SO4)
  5. customrotary evaporated (75° C.)

Sources & evidence

ORD record
ord-6ed9d8e09e554b18915a90e2dc679957
Source dataset
uspto-grants-2007_09
Patent number
US07268166B2

Reaction notes

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