Chlorotrimethylsilane → (2-Bromo-4-(4-ethoxybenzyl)benzyloxy)trimethylsilane

HRID 1716951Notes

Reaction equation

HRID 1716951 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:18][OH:19].CN1CCOCC1.[CH3:27][Si:28](Cl)([CH3:30])[CH3:29].CCOC(C)=O>C1COCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:18][O:19][Si:28]([CH3:30])([CH3:29])[CH3:27]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 59013454(2-Bromo-4-(4-ethoxybenzyl)phenyl)methanol

Product 1

HCID 59013485(2-Bromo-4-(4-ethoxybenzyl)benzyloxy)trimethylsilane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a cooled solution (−10° C.) of (2-bromo-4-(4-ethoxybenzyl)phenyl)methanol (0.137 g, 0.43 mmol) and N-methylmorpholine (0.1 mL, 0.9 mmol) in 2 mL of THF under N2, was added dropwise trimethylsilyl chloride. One hour later, the reaction was allowed to stir at 35° C. for 5 h and then stirred at 20° C. overnight. After dilution with AcOEt, the mixture was cooled to 0° C. prior to cautiously adding H2O at a rate such that the temperature did not exceed 10° C. The organic layer was separated and washed with aqueous KH2PO4, H2O, and brine. The volatiles were removed using a rotary evaporator to yield the title compound, which was used in the next step without further purification.

Workup

  1. customOne hour
  2. stirringstirred at 20° C. overnight
  3. customdid not exceed 10° C
  4. customThe organic layer was separated
  5. washwashed with aqueous KH2PO4, H2O, and brine
  6. customThe volatiles were removed
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-56211f1fe9714583a0963aae09ce4d1f
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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