Potassium tert-butoxide → HCID 67774918, compound

HRID 705931Notes

Reaction equation

HRID 705931 reaction equation
[CH3:1]C([O-])(C)C.[K+].[Cl:7][C:8]1[CH:22]=[C:21]([F:23])[C:11]([O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[C:10]([F:24])[CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:7][C:8]1[CH:22]=[C:21]([F:23])[C:11]([O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[CH2:1])=[CH:15][CH:14]=2)=[C:10]([F:24])[CH:9]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86666217HCID 86666217, compound

Product 1

HCID 67774918HCID 67774918, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (8.7 g, 24.35 mmol) and KOt-Bu (3.4 g, 30.3 mmol) in dry THF (20 mL), which was stirred at room temperature for 1 h under nitrogen, was added a solution of 4-(4-chloro-2,6-difluorophenoxy)benzaldehyde (5.4 g, 20.10 mmol) in THF (8 mL). The mixture was stirred at room temperature overnight, and quenched with water. The aqueous phase was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (2.6 g, 9.75 mmol, 48.5% yield). LCMS: rt=4.06 min, [M+H+]=267

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customquenched with water
  3. extractionThe aqueous phase was extracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via flash chromatography

Sources & evidence

ORD record
ord-6c314fcb347e4fb3921a9175a76fd309
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…