Hydrochloric Acid → (2-Allyl-4-bromo-6-methoxyphenoxy)triisopropylsilane

HRID 1698734Notes

Reaction equation

HRID 1698734 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([O:11][CH3:12])[C:5]=1[OH:13])[CH:2]=[CH2:3].N1C=CN=C1.Cl[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22].Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([O:11][CH3:12])[C:5]=1[O:13][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 574077562-Allyl-4-bromo-6-methoxyphenol

Product 1

HCID 67097015(2-Allyl-4-bromo-6-methoxyphenoxy)triisopropylsilane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

After dissolving 3 g of 2-allyl-4-bromo-6-methoxy-phenol [CAS No. 352019-92-2] in 10 ml of DMF, 1.3 g of imidazole and 2 g of chlorotriisopropylsilane were added and the mixture was stirred at 50° C. for 4 hours. Next, 1N hydrochloric acid was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give (2-allyl-4-bromo-6-methoxyphenoxy)triisopropylsilane.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationThe desiccating agent was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cf0a1b3576304ae5900c6c6903e6f58e
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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