Ethyl Bromide → (3-Ethoxy-5,6-difluoronaphthalen-2-yl)trimethylsilane

HRID 1873321Notes

Reaction equation

HRID 1873321 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[C:7]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:8]([OH:13])=[CH:9]2)=[CH:4][CH:3]=1.Br[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[CH2:19]([O:13][C:8]1[C:7]([Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][C:5]2[C:10]([CH:9]=1)=[C:11]([F:12])[C:2]([F:1])=[CH:3][CH:4]=2)[CH3:20]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 581519377,8-Difluoro-3-trimethylsilanylnaphthalen-2-ol

Product 1

HCID 58151894(3-Ethoxy-5,6-difluoronaphthalen-2-yl)trimethylsilane

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

54.7 g (about 0.12 mol) of 7,8-difluoro-3-trimethylsilanylnaphthalen-2-ol are stirred at 80° C. for 19 h together with 19.5 ml (0.26 mol) of bromoethane and 34.5 g (0.25 mol) of potassium carbonate in 400 ml of ethyl methyl ketone. The batch is filtered, and the residue is washed with ethyl methyl ketone. The filtrate is concentrated, and the residue is taken up in MTBE. The solution is washed with water and sat. sodium chloride soln. and dried using sodium sulfate. The residue remaining after removal of the solvent is purified by column chromatography (SiO2, toluene:ethyl acetate=9:1), giving (3-ethoxy-5,6-difluoronaphthalen-2-yl)trimethylsilane as a dark-brown solid.

Workup

  1. filtrationThe batch is filtered
  2. washthe residue is washed with ethyl methyl ketone
  3. concentrationThe filtrate is concentrated
  4. washThe solution is washed with water and sat. sodium chloride soln
  5. customand dried
  6. customafter removal of the solvent
  7. customis purified by column chromatography (SiO2, toluene:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-156dac9c313249acadc8205f37becccb
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

Loading…