Hydrochloric Acid → HCID 17604266, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl (4-bromo-2-formylphenoxy)acetate (Example 1, 6.00 g, 21.0 mmol) in 200 mL abs EtOH was stirred under Ar and the mixture was cooled to 0° C. To this mixture was added NaBH4 (199 mg, 5.24 mmol) in portions. The reaction was stirred for 1 hour where TLC (25% EtOAc/hexanes) revealed complete reaction. At this point, 1 N HCl was added dropwise until slightly acidic and the EtOH was removed under reduced pressure. Water (100 mL) was added and the reaction transferred to a separatory funnel where it was extracted 3×100 mL with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and removed in vacuo to provide the product (5.41 g, 89%) as a pure white solid. 1H-NMR (acetone-d6, δ): 1.24 (t, 3H), 4.21 (q, 2H), 4.76 (s, 2H), 4.85 (s, 2H), 6.98 (d, 1H), 7.46 (dd, 1H); 7.61 (d, 1H); LRMS (GC/MS/EI) 308 [M]+.

Provenance & Evidence