Water → 1286216-61-2

HRID 594282Notes

Reaction equation

HRID 594282 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[O:6].[B-](F)(F)(F)[F:14].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.O.CCOCC>CC#N>[F:14][C:10]1[C:3]([O:2][CH3:1])=[C:4]([C:7]([O:11][CH3:12])=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 964042,6-DimethoxybenzaldehydeHCID 2724933Selectfluor

Product 1

HCID 840495531286216-61-2

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Commercially available 2,6-dimethoxybenzaldehyde (3.500 g; 21.10 mmol) was added to a suspension of Selectfluor (8.208 g; 23.20 mmol) in MeCN (35 ml), and the resulting mixture was stirred at rt, under nitrogen, for 16 h. Water and Et2O were added and the aq. layer was further extracted with Et2O. The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=4/1) afforded 3-fluoro-2,6-dimethoxybenzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.60 min.; [M+H]+: 185.10 g/mol.

Workup

  1. extractionthe aq. layer was further extracted with Et2O
  2. dry with materialThe mixed organic layers were dried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by FC (heptane/AcOEt=4/1)

Sources & evidence

ORD record
ord-995135f3665d49feafdddd4858299646
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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