Tetrahydrofuran → HCID 66825615, compound

HRID 474638Notes

Reaction equation

HRID 474638 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:12]=2[C:13]#[N:14])=[CH:6][C:5]=1[C:21]([F:24])([F:23])[F:22].[CH2:25]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:16]([CH:19]=[CH2:25])=[CH:15][C:12]=2[C:13]#[N:14])=[CH:6][C:5]=1[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86666201Benzonitrile, 2-[4-chloro-3-(trifluoromethyl)phenoxy]-5-formyl-

Product 1

HCID 66825615HCID 66825615, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a solution of NaH (0.798 g, 19.96 mmol) in dry THF (15 mL) was added methyltriphenylphosphonium bromide (7.13 g, 19.96 mmol). The mixture was stirred at room temperature for 0.5 h. Then 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-formylbenzonitrile (5.0 g, 15.35 mmol) was added. Stirring continued for 1.5 h, and the mixture was quenched by ice water. THF was removed by evaporation; the aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound (1.8 g, 5.56 mmol, 36.2% yield).

Workup

  1. stirringStirring
  2. waitcontinued for 1.5 h
  3. customthe mixture was quenched by ice water
  4. customTHF was removed by evaporation
  5. extractionthe aqueous layer was extracted with DCM
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-db6c85402d914284a45506163442fd60
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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