Chlorotrimethylsilane → HCID 13725305, compound

HRID 637911Notes

Reaction equation

HRID 637911 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11](Br)[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]=1Br)[CH3:2].[Li].[CH3:16][Si:17](Cl)([CH3:19])[CH3:18].C(Br)CCC>O.CO>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([Si:17]([CH3:19])([CH3:18])[CH3:16])[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]=1[Si:17]([CH3:19])([CH3:18])[CH3:16])[CH3:2]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8002Butyl bromideHCID 3028194LithiumHCID 11232556HCID 11232556, compound

Product 1

HCID 13725305HCID 13725305, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To 32.4 g (0.1 mol) of 2,5-dibromohydroquinone diethyl ether were successively added 160 ml of diether ether, 2.8 g (0.4 gram-atom) of metallic lithium and 21.7 g (0.2 mol) of trimethylsilyl chloride, and the mixture was stirred under a nitrogen stream at 20° to 23° C. 27.4 g (0.2 mol) of butyl bromide was added dropwise to the mixture over a period of 1 hour, and the stirring was continued for an additional one hour while heating at 35° C. After cooling with ice, 50 ml of methanol was added thereto, followed by stirring. The reaction mixture was poured into water, and was extracted with 200 ml of ethyl acetate. The ethyl acetate layer was washed with 200 ml of a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to dryness and crystallized from acetonitrile. Recrystallization from acetonitrile gave 15.5 g (yield: 50%) of 2,5-bis(trimethylsilyl)hydroquinone diethyl ether having a melting point of 129° C.

Workup

  1. additionwas added
  2. stirringby stirring
  3. extractionwas extracted with 200 ml of ethyl acetate
  4. washThe ethyl acetate layer was washed with 200 ml of a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated to dryness
  8. customcrystallized from acetonitrile
  9. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-2325451d8d6c4123acd40fad032cba54
Source dataset
uspto-grants-1985_12
Patent number
US04559297

Reaction notes

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