Imidazole → 4-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzene

To a solution of [2-(4-bromophenoxy)ethanol (10.0 g, 46 mmol) in 150 mL dry dimethylformamide (30 mL) was added t-butyldimethylsilyl chloride (8.34 g, 55 mmol) and imidazole (7.82 g, 115 mmol). Additional dimethylformamide (20 mL) was used to wash these materials into the reaction flask. The resulting solution was stirred overnight at rt with a Newman tube. It was poured onto water (200 mL) and extracted with ether (3×75 mL). The combined extracts were washed with 0.5N HCl (200 mL), sat. NaHCO3 (200 mL), water (4∴150 mL), and sat. NaCl (200 mL), dried over MgSO4, and filtered. The solvent was removed under reduced pressure on a rotary evaporator to give the crude product (16.5 g; >100%). 1H NMR (CDCl3) δ7.34 (2H, d, J=8.9), 6.78 (2H, d, J=8.9), 4.00-3.93 (4H, m), 0.89 (9H, s), 0.08 (6H, s). 13C NMR (CDCl3) δ158.1, 132.2, 116.4, 112.8, 69.6, 61.9, 25.9, 18.4. FDMS (m/e) 330 (M+, 79Br). It was used as 100% without purification.

1. washto wash these materials into the reaction flask
2. additionIt was poured onto water (200 mL)
3. extractionextracted with ether (3×75 mL)
4. washThe combined extracts were washed with 0.5N HCl (200 mL), sat. NaHCO3 (200 mL), water (4∴150 mL), and sat. NaCl (200 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customThe solvent was removed under reduced pressure on a rotary evaporator

ORD record

ord-b6b694a4cf674f07bc202793a5bc7be6

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05686254