Acetovanillone → HCID 86633101, compound

HRID 1012205Notes

Reaction equation

HRID 1012205 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[CH2:5]Br.[CH3:17][C:18]([C:20]1[CH:28]=[CH:27][C:25]([OH:26])=[C:22]([O:23][CH3:24])[CH:21]=1)=[O:19].CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[CH2:5][O:26][C:25]1[CH:27]=[CH:28][C:20]([C:18](=[O:19])[CH3:17])=[CH:21][C:22]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 2214AcetovanilloneHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5188712,4-Bis(trifluoromethyl)benzyl bromide

Product 1

HCID 86633101HCID 86633101, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a N2 purged flask was added 2,4-bis-trifluoromethyl benzyl bromide (2.21 g, 7.20 mmol), acetovanillone (1.32 g, 7.92 mmol), and DMF (15 mL). To the reaction solution was added fine mesh K2CO3 (3 equiv, 21.6 mmol). The reaction was allowed to stir at 70° C. for 1 h, then at 60° C. for 14 h. The reaction solution was then diluted with EtOAc (150 mL), filtered through a Buchner funnel, washed with sat'd NH4Cl (70 mL×2) washed with sat NaCl (50 mL), dried over Na2SO4, and then filtered and concentrated in vacuo to provide a crude product (2.8 g, 99% yield).

Workup

  1. waitat 60° C. for 14 h
  2. filtrationfiltered through a Buchner funnel
  3. washwashed with sat'd NH4Cl (70 mL×2)
  4. washwashed with sat NaCl (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-067c04bc93814b388b49b48ddc73f6e4
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

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