Imidazole → (4-Bromo-phenoxy)-triisopropylsilane

HRID 2252390Notes

Reaction equation

[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.[CH:9]([Si:12](Cl)([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])([CH3:11])[CH3:10].N1C=CN=C1>C(Cl)Cl.CCOCC>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][Si:12]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:9]([CH3:11])[CH3:10])=[CH:1][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of p-bromophenol (5) (4.0 g, 23.1 mmol) in DCM (40 ml) was added triisopropylsilyl chloride (5 ml, 23.4 mmol). The reaction mixture was cooled to 0° C. and imidazole (3.94 g, 57.9 mmol) was added and the mixture was stirred at 0° C. for 30 minutes then allowed to warm to ambient temperature over 12 hours. The reaction mixture was diluted with ether and sequentially washed with 0.5 M HCl (2×), sat. aq. NaHCO3, water and brine then dried over MgSO4. The crude product was purified by bulb to bulb distillation (boiling point: 149-150° C. at 2.0 mmHg) to give 6 as a clear oil (6.23 g, 82% yield): 1H-NMR (400 MHz, chloroform-d) δ 7.30 (d, J=8.8 Hz, 2 H), 6.75 (d, J=8.8 Hz, 2 H), 1.24 (septet, J=7.2 Hz, 3 H), 1.09 (d, J=7.2 Hz, 18 H); 3C-NMR (100 MHz, chloroform-d) δ 155.2, 132.2, 121.7, 113.2, 17.8, 12.6; FTIR (thin film) 2945, 2892, 2867, 1586, 1487, 1274, 909, 883, 828, 732 cm−1; HRMS (EI+) for C15H25BrOSi calcd. 328.0858 found 328.0844.

Workup

temperatureto warm to ambient temperature over 12 hours
washsequentially washed with 0.5 M HCl (2×), sat. aq. NaHCO3, water and brine
dry with materialthen dried over MgSO4
distillationThe crude product was purified by bulb to bulb distillation (boiling point: 149-150° C. at 2.0 mmHg)

Sources & evidence

ORD record: ord-c6c38f530f624aa5b640ffda359fbed7
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07321065B2

Reaction notes

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