2,3,5,6-Tetrafluorophenol → Diphenyl carbonate

HRID 1432355Notes

Reaction equation

HRID 1432355 reaction equation
[F-].[K+].F[C:4]1[C:9](F)=[CH:8][C:7](F)=[C:6](F)[C:5]=1[OH:13].F[C:15]1[CH:20]=[C:19](F)[CH:18]=[C:17](F)[C:16]=1[OH:23].FC1C(F)=CC=C(F)[C:26]=1[OH:33].BrC(Br)=O>CO.C1COCC1.CN(C)C=O>[O:13]([C:26]([O:23][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:15]=1)=[O:33])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:4]=1

Participants

9

Reactant 5

HCID 698582,3,5,6-TetrafluorophenolHCID 79057Carbonyl bromideHCID 5179882,3,6-TrifluorophenolHCID 5199742,4,6-TrifluorophenolHCID 522689Potassium Fluoride3×

Product 1

HCID 7597Diphenyl carbonate

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In scheme III above, the following abreviations are used: KF is potassium fluoride; DMF is N,N-dimethylformamide; ArOH is either 2,3,5,6-tetrafluorophenol, 2,4,6-trifluorophenol or 2,3,6-trifluorophenol; THF is tetahydrofuran; MeOH is methanol. Commercially available bromoketone D is reacted with the appropriatly substituted fluorophenol and potassium fluoride to give phenoxy ketone E. The ketone is then reduced with sodium borohydride to give the alcohol F, which is hydrogenated using palladium on carbon as catalyst to give the amino alcohol B (in formula I, Y=fluoro-substituted phenoxy).

Sources & evidence

ORD record
ord-4e795b054f16466097325daa675da606
Source dataset
uspto-grants-2009_11
Patent number
US07612091B2

Reaction notes

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