4-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde → 1-Chloro-2-(trifluoromethyl)-4-(4-vinylphenoxy)benzene

HRID 474561Notes

Reaction equation

HRID 474561 reaction equation
[CH2:1]([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)=[CH:9][C:8]=1[C:22]([F:25])([F:24])[F:23]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[CH2:1])=[CH:16][CH:15]=2)=[CH:9][C:8]=1[C:22]([F:25])([F:24])[F:23]

Participants

5

Reactant 2

HCID 866661874-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 668258371-Chloro-2-(trifluoromethyl)-4-(4-vinylphenoxy)benzeneYield 78%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

An alternative synthesis was provided to prepare the compound of D21: To a suspension of methyltriphenylphosphonium bromide (64.7 g, 181 mmol) in anhydrous tetrahydrofuran (THF) (20 mL) was added dropwise n-butyllithium (113 mL, 181 mmol) under −78° C. over 30 mins. The reaction mixture was stirred for 1 h, and then was added a solution of 4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzaldehyde (36.3 g, 121 mmol) in anhydrous tetrahydrofuran (15 ml). The reaction mixture was warmed slowly to room temperature and stirred overnight at room temperature. The mixture was quenched with water and extracted with ethyl acetate. The organic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude sample was purified by silica gel column (220 g) using hexane/ethyl acetate (20:1) as eluent to afford the title compound (28 g, 94 mmol, 78% yield) LCMS: rt=4.29 min.

Workup

  1. customAn alternative synthesis
  2. customwas provided
  3. customto prepare the compound of D21
  4. stirringstirred overnight at room temperature
  5. customThe mixture was quenched with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase was dried with anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe crude sample was purified by silica gel column (220 g)

Sources & evidence

ORD record
ord-f666866bce5a4f21be3626642713c9b3
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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