Boron tribromide → HCID 66642898, compound

To a stirred solution of methyl 3,5-dichloro-4-(4′-methoxyphenoxy)benzoate (1.5 g, 4.5 mmol) in CH2Cl2 (50 mL) at −78° C. was added BBr3 (11.4 mL, 11.4 mmol, 1 M solution in CH2Cl2). The reaction mixture was stirred at room temperature for 14 h, poured into ice water (100 mL) and stirred for 1 h. The reaction mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was recrystallized from CH2Cl2, filtered and dried under reduced pressure to afford 3,5-dichloro-4-(4′-hydroxyphenoxy)benzoic acid as a brown solid (1.02 g, 75%): mp 163-165° C.; 1H NMR (300 MHz, DMSO-d6): δ 9.02 (bs, 1H), 8.0 (s, 2H), 6.67 (m, 4H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (2:3); Rf=0.3.

1. stirringstirred for 1 h
2. extractionThe reaction mixture was extracted with ethyl acetate (2×100 mL)
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude product was recrystallized from CH2Cl2
8. filtrationfiltered
9. customdried under reduced pressure

ORD record

ord-d2130a543e87438c966b55dae55ef5b3

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514419B2