Tetrahydrofuran → HCID 66825615, compound

HRID 705878Notes

Reaction equation

HRID 705878 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-24208542927641e88c55ea60e6e1bb25
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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