Sodium Azide → 2-Azido-1-(3-bromophenyl)ethan-1-ol

HRID 1160212Notes

Reaction equation

Br[CH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)[O:4][Si](C)(C)C.[N-:16]=[N+:17]=[N-:18].[Na+]>CS(C)=O>[N:16]([CH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)[OH:4])=[N+:17]=[N-:18]

Participants

Conditions

Temperature: 80 °C

Procedure

[2-Bromo-1-(3-bromo-phenyl)-ethoxy]-trimethyl-silane (5.85 g, 16.6 mmol and tetrabutyl sodium iodide (613 mg, 1.66 mmol) were dissolved in DMSO and sodium azide (2.16 g, 33.2 mmol) was slowly added. The mixture stirred at 80° C. for 4 hours and then at room temperature for 18 hours. The mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organics were washed with water brine and 1M HCl, then again with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with 5-10% ethyl acetate in hexanes. The title compound was isolated as a yellow oil (3.38 g, 83%). 1H NMR (300 MHz, CDCl3): 7.57 (s, 1H), 7.48 (d, 1H), 7.31-7.29 (m, 2H), 4.87 (m, 1H), 3.49 (d, 2H), 2.45 (d, 1H).

Workup

waitat room temperature for 18 hours
customThe mixture was quenched with saturated sodium bicarbonate
extractionextracted with ethyl acetate
washThe organics were washed with water brine and 1M HCl
dry with materialagain with water and brine, dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel
washeluting with 5-10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-a765f5e5f31043ddb60440427b903fe1
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816354B2

Reaction notes

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