t-Butyl 3-(2,6-dibromo-4-methoxyphenyl)-propionate → 3-(2,6-Dibromo-4-methoxyphenyl)-propionic acid

To a solution of t-butyl 3-(2,6-dibromo-4-methoxyphenyl)-propionate (1.32 g) in 3.6 mL of an isole was added 20 mL of trifluoroacetic acid dropwise. The resulting mixture was stirred for 20 min at room temperature, then concentrated. The resulting residue was redissolved in 20 mL of EtOAc and extracted with 40 mL of pH 4 buffer solution. The aqueous phase was extracted with 2×20 mL of EtOAc and the combined resulting organics were washed with 20 mL of brine, dried over MgSO4, and concentrated to yield 3-(2,6-dibromo-4-methoxyphenyl)-propionic acid as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 7.09 (s, 2H); 3.77 (s, 3H); 3.27 (m, 2H); 2.62 (m, 2H).

1. concentrationconcentrated
2. dissolutionThe resulting residue was redissolved in 20 mL of EtOAc
3. extractionextracted with 40 mL of pH 4 buffer solution
4. extractionThe aqueous phase was extracted with 2×20 mL of EtOAc
5. customthe combined resulting organics
6. washwere washed with 20 mL of brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-466a9f6269024e53843af1d52bb8a139

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06809199B2