Formaldehyde → HCID 87807692, compound

Participants

Reaction Steps

Methyl[3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenyl]acetate (2.0 g, 4.4 mmol), SnCl4 (25 μl, 0.2 mmol), trioctyl amine (0.77 mL, 1.76 mmol) and toluene (15 mL) were mixed in a reaction vial. After 20 minutes stirring at room temperature, paraformaldehyde (0.264 g, 8.8 mmol) was added to the reaction solution. The reaction vial was sealed and the temperature increased to 105° C. After 20 hours stirring, the reaction was quenched with ice-water and acidified with hydrochloric acid (1 N). Extraction with ethyl acetate, washing with brine, drying over Na2SO4 and concentration gave the crude product. The residue was purified on column (silica, gradient elution: n-heptane/ethyl acetate from 1:0 to 4:1) to give 1.08 g (51%) of methyl[3,5-dibromo-4-(3-formyl-4-hydroxy-5-isopropylphenoxy)phenyl]acetate.

Provenance & Evidence