HCID 22404751, compound → HCID 22404770, compound

HRID 440694Notes

Reaction equation

HRID 440694 reaction equation
[C:1]([C:3]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][C:6]([CH3:10])([CH3:9])[C:7]#[CH:8])#[N:2]>ClC1C=CC=CC=1Cl>[C:1]([C:3]1[C:4]2[O:5][C:6]([CH3:10])([CH3:9])[CH:7]=[CH:8][C:11]=2[CH:12]=[CH:13][C:14]=1[F:15])#[N:2]

Participants

3

Reactant 1

HCID 22404751HCID 22404751, compound

Product 1

HCID 22404770HCID 22404770, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

One thousand mL of stirred, 1,2-dichlorobenzene was heated to 180 ° C., and a solution of 75.0 grams (0.37 mole) of 3-(2-cyano-3-fluorophenoxy)-3-methyl-1-butyne in 100 mL of 1,2-dichlorobenzene was added dropwise. Upon completion of the addition, the reaction mixture was stirred at 180° C. for one hour, after which the reaction mixture was cooled and subjected to column chromatography on silica gel. The 1,2-dichlorobenzene solvent was separated by elution with hexane. The product was removed from the column by elution with methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 37.0 of 8-cyano-2,2-dimethyl-7-fluoro-2H-1-benzopyran, mp 99°-101° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction mixture was stirred at 180° C. for one hour
  3. temperatureafter which the reaction mixture was cooled
  4. customThe 1,2-dichlorobenzene solvent was separated by elution with hexane
  5. customThe product was removed from the column by elution with methylene chloride
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a6c13a159ab747afaac4bbd26795a15d
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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