Ammonium Chloride → HCID 67002199, compound

HRID 558440Notes

Reaction equation

HRID 558440 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8]P(=O)(OCC)OCC)=[CH:6][CH:5]=1.[Br:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH:30]=O.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C=O)C.O>[Br:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH:30]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:19])[F:20])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 225749024-Bromo-3-formylbenzonitrileHCID 23665647Potassium tert-butoxideHCID 57744084HCID 57744084, compound

Product 1

HCID 67002199HCID 67002199, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-25 °C

Procedure

Diethyl (4-trifluoromethoxybenzyl)phosphonate (7.8 g) was dissolved in 100 mL of DMF, 5.0 g of 4-bromo-3-formyl-benzonitrile was added, and the mixture was cooled to −25° C. Potassium tert-butoxide (6.4 g) was added, and the mixture was stirred for 2 hours at −25° C. To the reaction mixture, 100 mL of a saturated aqueous solution of ammonium chloride and 100 mL of water were added, and the mixture was extracted 3 times with ethyl acetate (100 mL). The respective organic layers were combined, whereafter the combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The magnesium sulfate was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to 100 g silica gel column chromatography to obtain 3.9 g of 4-bromo-3-[2-(4-trifluoromethoxy-phenyl)-vinyl]-benzonitrile as a crude product with the use of an eluant (ethyl acetate and n-hexane, 1:10).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate (100 mL)
  2. washwas washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. customThe magnesium sulfate was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce0b6dcb9db348808ff8964fbd904482
Source dataset
uspto-grants-2011_11
Patent number
US08063046B2

Reaction notes

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