1,1,1-Trifluoro-N-phenylmethanesulfonamide → Ethyl 3-chloro-4-(trifluoromethylsulfonyloxy)benzoate

HRID 2098899Notes

Reaction equation

HRID 2098899 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C1C=CC(N[S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 12652105Ethyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 57467588Ethyl 3-chloro-4-(trifluoromethylsulfonyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of ethyl 3-chloro-4-hydroxybenzoate (available from Aldrich) (5.00 g, 25.0 mmol), N-phenyltriflamide (9.30 g, 26.0 mmol) and TEA (4.2 mL, 30.0 mmol) in DCM (40 mL) with a catalytic amount of DMAP, was stirred at ambient temperature overnight. DCM (150 mL) was added, and the reaction mixture was washed with brine (30×3 mL), dried over MgSO4, and the solvent was removed under reduced pressure. The product T1.5 was used in the next step without further purification. MS ESI (pos.) m/e: 335.0 (M+Na)+.

Workup

  1. washthe reaction mixture was washed with brine (30×3 mL)
  2. dry with materialdried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe product T1.5 was used in the next step without further purification

Sources & evidence

ORD record
ord-8e2f460777f14bc0ad88eb2904c33301
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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