Trifluoroacetic anhydride → HCID 15817308, compound

HRID 865289Notes

Reaction equation

HRID 865289 reaction equation
FC1[C:7](OC)=[CH:6][CH:5]=[CH:4][C:3]=1[S:10][CH2:11][CH2:12]C(O)=O.FC(F)(F)[C:18]([O:20][C:21](=O)[C:22]([F:25])(F)F)=O.C([O-])([O-])=[O:30].[Na+].[Na+]>FC(F)(F)C(O)=O>[F:25][C:22]1[C:21]([O:20][CH3:18])=[CH:7][CH:6]=[C:5]2[C:4]=1[CH2:3][S:10][CH2:11][C:12]2=[O:30]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 54162170HCID 54162170, compound

Product 1

HCID 15817308HCID 15817308, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The acid from Step 5 (7.63 g, 33 mmol) was dissolved in trifluoroacetic acid (12 mL), treated with trifluoroacetic anhydride (4 mL) and stirred at room temperature (8 minutes). The reaction was poured into 10% Na2CO3 (50 mL) and extracted with ethyl acetate, washed with brine, dried over MgSO4 and concentrated in vacuo to give 8-fluoro-7-methoxyisothiochroman-4-one (5.42 g, 77%) as a brown solid: mp 85°-92° C.; 1H NMR (CDCl3) 300 MHz 7.83 (d, J=8.9 Hz, 1H) 7.19 (t, J=8.5 Hz, 1H) 4.01 (s, 2H) 3.98 (s, 3H) 3.55 (s, 2H); 19F NMR (CDCl3) 300 MHz -141.24 (m).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c37d90c411e4f919600abb250afc4ca
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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