Imidazole → 2-[2-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethyl]benzene bromide

HRID 2372902Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].N1C=CN=C1.[CH3:16][Si:17](Cl)([CH3:24])[C:18]([CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.O.CCOCC>[Br-:1].[CH3:16][Si:17]([CH3:24])([C:18]([CH3:20])([CH3:19])[CH:21]([CH3:23])[CH3:22])[O:6][CH2:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Bromophenethyl alcohol (43.80 g, 217.9 mmol) was dissolved in anhydrous CH2Cl2 (200 mL) and imidazole (16.32 g, 239.6 mmol) was added and stirred under argon 0° C. Dimethylthexylsilyl chloride (42.83 g, 239.6 mmol) was added dropwise and the reaction mixture was stirred for three days at room temperature. It was diluted with H2O (50 mL) and ether (100 mL) and partitioned. The aqueous layer was extracted with ether (2×100 mL). The combined organic layers were washed with 5% aqueous HCl (1 time), H2O (1 time), aqueous NaHCO3 (1 time), H2O (1 time), and brine, then dried (MgSO4) and concentrated in vacuo to obtain a yellow oil. The crude product was Kugelrohr distilled (55°-80° ) under oil pump vacuum to give the purified title compound.

Workup

stirringthe reaction mixture was stirred for three days at room temperature
custompartitioned
extractionThe aqueous layer was extracted with ether (2×100 mL)
washThe combined organic layers were washed with 5% aqueous HCl (1 time), H2O (1 time), aqueous NaHCO3 (1 time), H2O (1 time), and brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto obtain a yellow oil
distillationdistilled (55°-80° ) under oil pump vacuum
customto give the
custompurified title compound

Sources & evidence

ORD record: ord-fd88063746944a8e8c14eb51e273db69
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05100889

Reaction notes

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