Bromoacetyl bromide → HCID 57871956, compound

Participants

Reaction Steps

To a solution of 4 (50 mg, 0.27 mmol) in CH2Cl2 (3 mL) was added sat. NaHCO3 (3 mL). Under stirring, bromoacetyl bromide (80 mg, 040 mmol) was added. The pH was controlled in the range 8-9 by adding solid NaHCO3. The reaction was stirred at rt for 15 min. CH2Cl2 (5 mL) was added and the reaction mixture was extracted 5×3 mL CH2Cl2. The organic layers were combined, washed with brine, dried with Na2SO4. The solvent was evaporated and the residue was purified by FCC to afford 5 as clear oil (65 mg, 78%). 1H NMR (400 MHz, CDCl3): δ 2.42 (t, J=2.4 Hz, 1H), 3.48 (dd, J=5.2, 5.2 Hz, 2H) 3.57 (t, J=5.2 Hz, 2H), 3.62 (m, 4H), 3.66-3.70 (m, 4H), 3.85 (s, 2H), 4.18 (d, J=2.4 Hz, 2H). 6.91 (bs, 1H). 13C NMR (100 MHz, CDCl3): δ 29.35, 40.11, 58.65, 69.32, 69.56, 70.53, 70.61, 70.76, 74.90, 79.73, 165.86. ESIMS calcd for C11H18BrNNaO4 [M+Na]+ 330.03, 332.03, found: 330.33, 332.46.

Provenance & Evidence