Trifluoromethanesulfonic anhydride → Trifluoro-methanesulfonic acid 4-fluoro-2-(morpholine-4-sulfonyl)-phenyl ester

HRID 1971836Notes

Reaction equation

HRID 1971836 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:3]=1.[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:18])=[C:4]([S:9]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)(=[O:10])=[O:11])[CH:3]=1

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 581269904-Fluoro-2-(morpholine-4-sulfonyl)-phenol

Product 1

HCID 58127026Trifluoro-methanesulfonic acid 4-fluoro-2-(morpholine-4-sulfonyl)-phenyl esterYield 79.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-2-(morpholinosulfonyl)phenol (0.4 g, 1.5 mmol) and DMAP (0.28 g 2.29 mmol) in CH2Cl2(10 ml), Tf2O (0.93 ml 5.5 mmol) was added dropwise at 0° C. The mixture was stirred at room temperature for 4 h, after which the mixture was washed with hydrochloric acid (1N, 20 ml) and then extracted with EA. The extracts were combined, washed with brine, dried over sodium sulfate and evaporated into dryness. The resulting residue was purified by column chromatography using PE/EA (10/1) as eluent to give the desired product (469 mg, yield 78%).

Workup

  1. washafter which the mixture was washed with hydrochloric acid (1N, 20 ml)
  2. extractionextracted with EA
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated into dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-800cd6ab29a14f4daacf2d1bd5918ea4
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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