4-Hydroxybenzaldehyde → HCID 86685856, compound

HRID 1629765Notes

Reaction equation

HRID 1629765 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17].C([O-])([O-])=O.[K+].[K+]>CC#N>[F:17][C:16]([F:19])([F:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 138454716-Bromo-1,1,1-trifluorohexane

Product 1

HCID 86685856HCID 86685856, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-hydroxybenzaldehyde (488 mg, 4 mmol) and 6-bromo-1,1,1-trifluorohexane (657 mg, 3 mmol) in MeCN (10 mL) was added K2CO3 (829 mg, 6.00 mmol). The resulting mixture was reflux overnight. Insoluble material was filtered off and rinsed with MeCN. The combined filtrate was concentrated to afford a white solid. This white solid was partitioned between EtOAc and 1 N NaOH solution. The organic layer was separated, washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated to afford Intermediate 8A as a clear liquid. LCMS Anal. Calc'd for C13H15F3O2 260.10, found [M+H] 261.0.

Workup

  1. temperatureThe resulting mixture was reflux overnight
  2. filtrationInsoluble material was filtered off
  3. washrinsed with MeCN
  4. concentrationThe combined filtrate was concentrated
  5. customto afford a white solid
  6. customThis white solid was partitioned between EtOAc and 1 N NaOH solution
  7. customThe organic layer was separated
  8. washwashed with sat'd NH4Cl
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-05a7fdcc58bf4a028256306f73308424
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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