Carbon tetrabromide → HCID 68632463, compound

Participants

Reaction Steps

Compound 10 (651 mg, 1.50 mmol) and carbon tetrabromide (628 mg, 1.88 mmol) were dissolved in tetrahydrofuran (THF, 0.5 mL). Triphenylphosphine (498 mg, 1.88 mmol) was added to this solution portionwise over 5 min with stirring and additional amount of THF (0.5 mL) was added to the mixture. Reaction was monitored by TLC, which indicated that it was over in 10 min Solvent was removed at room temperature and the crude product was chromatographed (SiO2, hexane/EtOAc 2:1) to give 767 mg (1.55 mmol, >100%, less dry) of 35 as a clear colorless oil. Rf 0.74 (hexane/EtOAc 1:1); 1H NMR (400 MHz, CDCl3) 7.68 (m, 4H, H-2 of phenyl), 7.45-7.35 (m, 6H, H-3 and H-4 of phenyl), 3.81 (t, 2H, J=5.5 Hz, CH2CH2OSi), 3.79 (t, 2H, J=7.1 Hz, CH2CH2Br), 3.65 (m, 8H, (OCH2CH2)2OCH2CH2OSi), 3.61 (t, 2H, J=5.3 Hz, CH2CH2OSi), 3.45 (t, 2H, J=6.4 Hz, CH2CH2Br), 1.05 (s, 9H, C(CH3)3); MS (ESI) Calcd for C24H35BrO4SiNa (M+Na+): 517.1. Found: 517.1.

Provenance & Evidence