Sodium Hydroxide → HCID 58764125, compound

HRID 2387043Notes

Reaction equation

HRID 2387043 reaction equation
C[Si](C)(C)[C:3]([F:6])([F:5])[F:4].Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[O:18][CH3:19].[F-].[K+].[OH-].[Na+]>CN(C=O)C.CN1C(=O)CCC1.[Cu]I.O>[CH3:19][O:18][C:12]1[C:13]([CH2:17][C:3]([F:6])([F:5])[F:4])=[CH:14][CH:15]=[CH:16][C:11]=1[CH3:10]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 144337981-(Bromomethyl)-2-methoxy-3-methylbenzene

Product 1

HCID 58764125HCID 58764125, compoundYield 90.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
55 °C

Procedure

Trimethyl(trifluoromethyl)silane (25.39 mL, 162.5 mmol) was added to a stirred mixture of 1-bromomethyl-2-methoxy-3-methyl-benzene (19 g, 65 mmol), KF (9.44 g, 162.5 mmol), CuI (37.10 g, 195 mmol) in DMF (75 mL) and NMP (75 mL). The reaction mixture was heated to 55° C. under N2 for 15 hours. The mixture was poured into water, made basic with 1N NaOH and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a black oil. Flash column chromatography (0% to 60% EtOAc in hexanes) gave the product as a yellow oil (12.0 g). LCMS: APCI−VE=203

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a black oil

Sources & evidence

ORD record
ord-dfb29424743a485f82232c10e7c4b9cf
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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