Isopropyl iodide → HCID 18782474, compound

HRID 1417547Notes

Reaction equation

HRID 1417547 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH:8]([CH3:10])[CH3:9].[Br:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[OH:22]>CN(C=O)C>[Br:11][C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][C:13]=1[O:22][CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 27611682-Bromo-4-(trifluoromethyl)phenol

Product 1

HCID 18782474HCID 18782474, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Powdered potassium carbonate (1.72 g, 12.5 mmol) and 2-iodopropane (1.16 mL, 1.98 g, 11.6 mmol) were added to a solution of 2-bromo-4-(trifluoromethyl)phenol (2.00 g, 8.30 mmol) in DMF. The mixture was stirred overnight at RT and then partitioned between hexane (100 mL) and water (100 mL). The organic layer was washed with saturated aqueous sodium chloride (50 mL) and the aqueous layers were extracted in succession with hexane (50 mL). The organic layers were dried over sodium sulfate, decanted, and evaporated. The crude product was purified by flash column chromatography, eluting with hexane, to give the title compound. Mass spectrum (EI): m/z=282 (M+).

Workup

  1. custompartitioned between hexane (100 mL) and water (100 mL)
  2. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL)
  3. extractionthe aqueous layers were extracted in succession with hexane (50 mL)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. customdecanted
  6. customevaporated
  7. customThe crude product was purified by flash column chromatography
  8. washeluting with hexane

Sources & evidence

ORD record
ord-a58708bcc0f34032bc2395eaad2af0a8
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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