Fluorobenzene → 4,4'-Difluorobenzophenone

HRID 1194583Notes

Reaction equation

HRID 1194583 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClC1C=CC=CC=1Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10008FluorobenzeneHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 95824,4'-DifluorobenzophenoneYield 64%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
-12 °C

Procedure

0.113 mole) in orthodichlorobenzene at -14° C. was slowly added over 5 minutes a mixture of 4-fluorobenzoyl chloride (4.0 g., 0.025 mole) and fluorobenzene (2.4 g., 0.025 mole). The mixture was then maintained at -12° C. for one hour and then allowed to warm up to room temperature overnight then worked up as described in example 1. The crude 4,4'-difluorobenzophenone obtained (3.5 g., 64% yield) had a 90% purity with 0.5% ortho impurities and 5 other small impurity peaks by 19F NMR. 1 HNMR indicated 95% purity with 5% unreacted acid chloride.

Workup

  1. temperatureto warm up to room temperature overnight

Sources & evidence

ORD record
ord-005c10ffedd849be89cb2566a8c1ebf6
Source dataset
uspto-grants-1989_03
Patent number
US04814508

Reaction notes

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