Sodium Fluoride → 3-Bromo-4-fluorobenzoyl fluoride

HRID 1583889

Reaction equation

HRID 1583889 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[Br:11].[F-:12].[Na+].[F-:14].[K+]>C1S(=O)(=O)CCC1>[F:12][C:2]1[CH:10]=[CH:9][C:5]([C:6]([F:14])=[O:7])=[CH:4][C:3]=1[Br:11]

Participants

5

Reactant 3

HCID 5235Sodium FluorideHCID 522689Potassium FluorideHCID 202297303-Bromo-4-chlorobenzoyl chloride

Product 1

HCID 129227073-Bromo-4-fluorobenzoyl fluorideYield 79%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent2×

Procedure

1,270 g (5 moles) of 4-chloro-3-bromo-benzoyl chloride, 1,150 g of tetramethylenesulphone and 315 g (7.5 moles) of anhydrous sodium fluoride were warmed for 5 hours to 210° C., while stirring. Thereafter, 435 g (7.5 moles) of anhydrous potassium fluoride, suspended in 1,150 g of tetramethylenesulphone, were added to the reaction mixture, and the latter was stirred for a further 7 hours at 210° C. The subsequent distillation gave 873 g (79% of theory) of 4-fluoro-3-bromobenzoyl fluoride (a starting material for Example 19).

Workup

  1. additionwere added to the reaction mixture
  2. stirringthe latter was stirred for a further 7 hours at 210° C
  3. distillationThe subsequent distillation

Sources & evidence

ORD record
ord-b653fc85bcfd4c4fa2e93031028595c4
Source dataset
uspto-grants-1985_11
Patent number
US04555370

Linked notes

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