Acetic Anhydride → HCID 178505439, compound

HRID 1983968Notes

Reaction equation

HRID 1983968 reaction equation
C(O)(O)CC.[Br:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([C:14]2C=[CH:21][CH:20]=[CH:19][C:15]=2C(Cl)=O)=[CH:9][C:8]=1[F:23].[OH:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26].C(OC(=O)C)(=O)C>C(OCC)C>[O-:27][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:26])=[O:24].[Br:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([C+:14]2[CH2:15][CH2:19][CH2:20][CH2:21][S:25]2)=[CH:9][C:8]=1[F:23]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 62406Trifluoromethanesulfonic acidHCID 134919PropanediolHCID 86620802HCID 86620802, compound

Product 1

HCID 178505439HCID 178505439, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

Propanediol (0.3 mole) is cooled under a nitrogen atmosphere to a temperature of 0° C. Then 4-bromo-3,5-difluorophenylbenzoylchloride (0.3 mole) are swiftly added with continuous stirring. The reaction mixture is then cooled to −10° C. and triflic acid (0.45 mole) is added. The reaction mixture is stirred further for 1 hour, then acetic anhydride (2 mole) is added maintaining the temperature below 5° C. After adding diethyl ether and stirring for 1 more hour at −10° C., 4-bromo-3,5-difluorophenyl-thianylium triflate is filtered off and washed with cold ether.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. stirringstirring for 1 more hour at −10° C.
  3. filtration4-bromo-3,5-difluorophenyl-thianylium triflate is filtered off
  4. washwashed with cold ether

Sources & evidence

ORD record
ord-4e2485d129184009bda3326929f6051a
Source dataset
uspto-grants-2009_06
Patent number
US07544400B2

Reaction notes

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