Sodium Hydroxide → 4-Bromo-2-methoxyphenol

A suspension of (20.7 g, 47.9 mmol, 1.0 eq) bis(2-methoxy-5-bromophenyl)carbonate in 250 ml methanol and 60 ml (120 mmol, 2.5 eq) of 2N NaOH was refluxed for 2 hours. The reaction mixture was cooled to room temperature, concentrated to a volume of ca 100 ml, and poured into 1 L of H2O. The pH was adjusted to 2 using 1N HCl. The acidic mixture was transferred to a separatory funnel, and extracted three times with ether. The ether extracts were combined and washed once with H2O, once with brine, and then dried over anhydrous sodium sulfate. Filtration, concentration and drying afforded 19.0 g of a white solid, which was recrystallized from petroleum ether to yield 17.63 g, 91% yield, of white prisms.

1. temperaturewas refluxed for 2 hours
2. concentrationconcentrated to a volume of ca 100 ml
3. additionpoured into 1 L of H2O
4. customThe acidic mixture was transferred to a separatory funnel
5. extractionextracted three times with ether
6. washwashed once with H2O, once with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationFiltration, concentration
9. customdrying

ORD record

ord-85885bf756c6419799ee2a01ba48613d

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05563143