4,4'-Difluorobenzophenone → HCID 14723979, compound

HRID 974477Notes

Reaction equation

HRID 974477 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[F:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1>O1CCCC1>[F:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)([OH:19])[CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 95824,4'-DifluorobenzophenoneHCID 788251,5-DimethyltetrazoleHCID 178418339Butyllithium

Product 1

HCID 14723979HCID 14723979, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 1,5-dimethyltetrazole (0.98 g, 10.0 mmoles) in tetrahydrofuran (20 mL) at -30° C. was added n-butyl lithium (4.7 mL of 2.14M solution, 10.0 mmoles). After stirring for 0.25 hour, the solution was cooled to -50° C. and 4,4'-difluorobenzophenone (1.74 g, 8.0 mmoles) was added. After stirring for 1 hr at -50° C. and 1 hour at -10° C., the reaction was quenched with 1N hydrochloric acid. The mixture was extracted with methylene chloride, dried and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with 40% (v/v) ethyl acetate in hexane to give 2.0 g of the title compound; m.p.=116°-118° C.

Workup

  1. stirringAfter stirring for 1 hr at -50° C. and 1 hour at -10° C.
  2. customthe reaction was quenched with 1N hydrochloric acid
  3. extractionThe mixture was extracted with methylene chloride
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with 40% (v/v) ethyl acetate in hexane

Sources & evidence

ORD record
ord-ee4b7efcaeb449a698a3062cd8738bc5
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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