Sulfolane → Neopentyl 3,5-dichloro-4-fluorobenzoate

HRID 2073373Notes

Reaction equation

HRID 2073373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:17])[C:15]=1Cl)[C:5]([O:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:6].[F-:18].[K+].S1(CCCC1)(=O)=O>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:17])[C:15]=1[F:18])[C:5]([O:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:6]

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 522689Potassium FluorideHCID 14692894HCID 14692894, compound

Product 1

HCID 14692895Neopentyl 3,5-dichloro-4-fluorobenzoateYield 63.3%

Reagents, catalysts & solvents 1

HCID 2724163Tetraphenylphosphonium BromideCatalyst

Procedure

The reaction was conducted in the same manner as in Example 1 for 6 hours by using 8.9 g (30 mmol) of neopentyl 3,4,5-trichlorobenzoate instead of neopentyl 2,3,4,5-tetrachlorobenzoate in Example 1, 2.6 g (45 mmol) of spray-dried potassium fluoride, 1.3 g (3 mmol) of tetraphenyl phosphonium bromide and 9 g of anhydrous sulfolane. The post-treatment was conducted in the same manner, followed by distillation under reduced pressure to obtain 5.3 g of neopentyl 3,5-dichloro-4-fluorobenzoate. Further, the distillation residue was subjected to silica gel column chromatography and eluted with benzene to obtain 2.0 g of neopentyl 3,5-dichloro-4-fluorobenzoate as slightly yellow plates. The combined yield was 87%. The physical properties are shown below.

Workup

  1. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3ad1298c9af74979a8927d48469275b7
Source dataset
uspto-grants-1990_04
Patent number
US04916253

Reaction notes

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