Selectfluor → 1,4-Dimethoxy-3-fluoro-2-naphthaldehyde

HRID 1527709Notes

Reaction equation

HRID 1527709 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH:15]=[O:16].[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([F:18])[C:4]=1[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 105848151,4-Dimethoxy-2-naphthaldehyde

Product 1

HCID 461800431,4-Dimethoxy-3-fluoro-2-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Aldehyde 27 (0.517 g, 2.39 mmol) was added to a flame-dried 50 mL round bottom flask under Argon, followed by Selectfluor (1.25 g, 3.37 mmol) and MeCN (20.0 mL). The reaction was then heated to reflux for 8 hours before being cooled and extracted with EtOAc. The organic layer was washed 3 times with brine, dried over MgSO4, filtered, and condensed to provide the crude aldehyde as a yellow solid. Following flash chromatography (3:1 CH2Cl2:hexanes) aldehyde 51 (0.254 g, 1.08 mmol, 45%) was obtained as a yellow solid.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 8 hours
  3. temperaturebefore being cooled
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed 3 times with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customcondensed

Sources & evidence

ORD record
ord-63c952c699e04631aca9f0c7d34125fb
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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