Chlorotrimethylsilane → [1-(3-Bromo-4-methoxyphenyl)cyclopropyloxy]trimethylsilane

HRID 406396Notes

Reaction equation

HRID 406396 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[Br:6][C:7]1[CH:8]=[C:9]([C:15]2([OH:18])[CH2:17][CH2:16]2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].C(N(CC)CC)C>C1COCC1.O>[Br:6][C:7]1[CH:8]=[C:9]([C:15]2([O:18][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:17][CH2:16]2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 626698761-(3-Bromo-4-methoxyphenyl)cyclopropanol

Product 1

HCID 66618984[1-(3-Bromo-4-methoxyphenyl)cyclopropyloxy]trimethylsilane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Trimethylsilyl chloride (6.54 ml) was added to a solution of 1-(3-bromo-4-methoxyphenyl)cyclopropanol (5.0 g) and triethylamine (8.61 ml) in THF (100 ml). The reaction mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (3.84 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-012c5307faf646d5a50f18d00ec9ef16
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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