Phosphoric Acid → 1-(Methanesulfonyl)-4-[4-(trifluoromethoxy)phenoxy]benzene

HRID 1700841Notes

Reaction equation

HRID 1700841 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.OP(O)(O)=O>O.CS(C)=O>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([O:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][C:15]([F:14])([F:24])[F:25])=[CH:18][CH:19]=2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 1004Phosphoric Acid2×HCID 14797Potassium HydroxideHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 102866141-(Methanesulfonyl)-4-[4-(trifluoromethoxy)phenoxy]benzeneYield 89.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of 1-fluoro-4-(methylsulfonyl)benzene (2.2 kg), KOH (906.3 g), 4-(trifluoromethoxy)phenol (2.364 kg) and DMSO (4.4 L) was heated to 90° C. and stirred until HPLC showed <0.5% starting material remained (about 10 hours). HPLC conditions: Zorbax SB-C8 4.6 mm×25 cm; mobile phase was a gradient of 70% water with 0.1% H3PO4/30% acetonitrile to 10% water with 0.1% H3PO4/90% acetonitrile over 15 minutes at a flow rate of 1.5 mL/min, followed by a five minute hold at 10/90; UV detection at 220 nM. Retention times: starting sulfone, 4.5 min; desired product, 7.8 min.

Workup

  1. custom(about 10 hours)
  2. customover 15 minutes

Sources & evidence

ORD record
ord-45650bfbfdae493f9e219df0128e96df
Source dataset
uspto-grants-2002_02
Patent number
US06350902B2

Reaction notes

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