Potassium Carbonate → HCID 86636415, compound

HRID 1471487Notes

Reaction equation

HRID 1471487 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:10]=[O:11].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.O>CN(C)C=O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[CH:10]=[O:11])=[CH:15][C:14]=1[CH2:20][OH:21]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 109097255-Cyano-2-fluorobenzaldehydeHCID 207854984-bromo-3-(hydroxymethyl)phenolHCID 22728543Water ethylacetate

Product 1

HCID 86636415HCID 86636415, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-fluoro-3-formylbenzonitrile (14.2 g, 96.0 mmol), 4-bromo-3-hydroxymethylphenol (19.4 g, 96 mmol), and potassium carbonate (15.2 g, 110 mmol) in N,N-dimethylformamide (200 mL) was stirred at 70° C. under nitrogen atmosphere for 2 h. The mixture was poured into ethyl acetate/water. The organic layer was washed with water twice and with brine, then dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column (3:1 to 7:3 hexane/ethyl acetate) to give 4-[4-bromo-3-(hydroxymethyl)phenoxy]-3-formylbenzonitrile (26.0 g, 82%).

Workup

  1. washThe organic layer was washed with water twice
  2. dry with materialwith brine, then dried on anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column (3:1 to 7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f33ffe9603c8453cb291019d8abf3ab8
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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