Hydrochloric Acid → 7,8-Dichloro-3-(trifluoroacetyl)thiochroman-4-one

HRID 865295Notes

Reaction equation

HRID 865295 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[Cl:13][C:14]1[C:23]([Cl:24])=[C:22]2[C:17]([C:18](=[O:25])[CH2:19][CH2:20][S:21]2)=[CH:16][CH:15]=1.Cl>CCOCC>[Cl:13][C:14]1[C:23]([Cl:24])=[C:22]2[C:17]([C:18](=[O:25])[CH:19]([C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[CH2:20][S:21]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 544217637,8-Dichlorothiochroman-4-one

Product 1

HCID 536483537,8-Dichloro-3-(trifluoroacetyl)thiochroman-4-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl trifluoroacetate (0.29 g, 2.0 mmol) was placed in a round bottom flask, and dissolved in ether (12 mL). To the stirred solution was added sodium methoxide (25%) (0.84 g, 3.9 mmol), followed by 7,8-dichlorothiochroman-4-one from Step 2 (0.42 g, 1.8 mmol). The reaction was stirred at room temperature overnight (19.4 hours) and treated with 3N hydrochloric acid. The organic layer was collected, washed with brine, dried over MgSO4, and concentrated in vacuo to give a brown oily solid which was used without purification in the next step.

Workup

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a brown oily solid which
  6. customwas used without purification in the next step

Sources & evidence

ORD record
ord-8a9568565907473cb0bb84d92ec2b08f
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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