Dichloromethane → 4-[[(Trifluoromethyl)sulfonyl]oxy]-1,3-benzenedicarboxylic acid dimethyl ester

HRID 2098914Notes

Reaction equation

HRID 2098914 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].C(Cl)Cl.C1C=CC(N[S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])=CC=1>CN(C1C=CN=CC=1)C>[F:30][C:29]([F:32])([F:31])[S:26]([O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 80087Dimethyl 4-hydroxyisophthalate

Product 1

HCID 120175464-[[(Trifluoromethyl)sulfonyl]oxy]-1,3-benzenedicarboxylic acid dimethyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a stirred solution of dimethyl 4-hydroxyisophthalate T9.1 (commercially available from Chem Service) (37.7 g, 179 mmol) in DCM (256 mL, 179 mmol) at 23° C. was added TEA (30 mL, 215 mmol), and a catalytic amount of DMAP. N-phenyltriflamide (70 g, 197 mmol) was then added, and stirring was continued at room temperature for 21 hours. The solvent was removed, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield T9.2 dimethyl 4-(trifluoromethylsulfonyloxy)isophthalate as a colorless oil (59.00 g, 96% yield). MS ESI (pos.) m/e: 360.0 (M+H2O)+, 343.0 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7cb92dd56deb45ab98aaa856a740a7d6
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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