HCID 86666216, compound → HCID 67776822, compound

HRID 705928Notes

Reaction equation

HRID 705928 reaction equation
[CH2:1]([Li])CCC.[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[CH:9][C:8]=1[O:22][C:23]([F:26])([F:25])[F:24]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[CH2:1])=[CH:14][CH:13]=2)=[CH:9][C:8]=1[O:22][C:23]([F:26])([F:25])[F:24]

Participants

5

Reactant 2

HCID 86666216HCID 86666216, compoundHCID 178418339Butyllithium

Product 1

HCID 67776822HCID 67776822, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of methyltriphenylphosphonium bromide (3.9 g, 10.92 mmol) in dry THF (20 mL) was added n-butyllithium (6.8 mL, 10.88 mmol) dropwise at −78° C. for 0.5 h, the mixture was stirred for 1 h, and then was added a solution of 4-(4-chloro-3-(trifluoromethoxy)phenoxy)benzaldehyde (2.8 g, 8.84 mmol) in THF (5 mL). The reaction was warmed slowly to room temperature, stirred for overnight, and quenched with water. The aqueous layer was extracted with DCM. The organic phase was dried with anhydrous Na2SO4, concentrated and purified via flash chromatography to afford the title compound (1.2 g, 3.81 mmol, 43.1% yield). LCMS: rt=4.42 min, [M+H+]=315

Workup

  1. stirringstirred for overnight
  2. customquenched with water
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialThe organic phase was dried with anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified via flash chromatography

Sources & evidence

ORD record
ord-e321de4c76084acc8d9f5ae1207b98e7
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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