Oxalyl chloride → HCID 21865381, compound

HRID 856993Notes

Reaction equation

HRID 856993 reaction equation
[C:1](=[O:3])=O.CC(C)=O.[Cl-].[Cl-].[Cl-].[Al+3].C(Cl)(=O)C(Cl)=O.[CH2:18]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1>C(=S)=S.C(Cl)(Cl)Cl.O>[F:26][C:22]1[CH:23]=[CH:24][C:25]2[C:1](=[O:3])[C:32]3[CH:31]=[CH:30][C:29]([F:33])=[CH:28][C:27]=3[CH2:18][CH2:19][C:20]=2[CH:21]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 4559651HCID 4559651, compoundHCID 6451240Aluminum(III) ChlorideHCID 18522661Acetone cardice

Product 1

HCID 21865381HCID 21865381, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6348Carbon DisulfideSolvent2×

Conditions

Temperature
35 °C

Procedure

To a cooled (dry-ice/acetone bath) suspension of anhydrous aluminium trichloride (5 eq, 45.82 g, 0.34 Mol) in carbon disulfide (450 ml) was added oxalyl chloride (4 eq, 23.58 ml) dropwise. The mixture was allowed to reach room temperature before the slow addition of 1,1′-(1,2-ethanediyl)bis[3-fluorobenzene](1 eq, 15.00 g) as a solution in carbon disulfide (20 ml). The mixture was heated overnight at 35° C. and diluted with chloroform (400 ml). The mixture was cooled (ice-bath) and water (400 ml) slowly added. The phases were separated, the aqueous phase extracted with chloroform and the combined organic phases dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (15:1 heptane/ethyl acetate) to afford 2,8-difluoro-10,11-dihydro-dibenzo[a,d]cycloheptene-5-one as a yellow solid (4.98 g, 29%).

Workup

  1. temperatureTo a cooled
  2. additionslowly added
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with chloroform
  5. dry with materialthe combined organic phases dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (15:1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-56a581268cc74cc0bbcb7db6ccf58902
Source dataset
uspto-grants-2006_12
Patent number
US07144890B2

Reaction notes

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