Sodium Hydroxide → HCID 58764125, compound

HRID 859654Notes

Reaction equation

HRID 859654 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 1 N 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-1216d8545290425b98d479d6ca277827
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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