Triethylsilane → 4-(4-Bromo-2-methylphenyl)butanoic acid

Temperature

90 °C

To a solution of 55A (542 mg, 2 mmol) in TFA (5 mL) was added triethylsilane (0.8 mL, 5 mmol) and the mixture heated at 90° C. for 7 h. The reaction was quenched with 1N NaOH (20 mL) and washed with EtOAc (20 mL). Aqueous layer was acidified to pH 1 with 1N HCl and extracted with EtOAc (2×20 mL). The combined organics were washed with brine (10 mL) and dried (MgSO4). The organic layer was concentrated in vacuo and the residue purified by flash chromatography (0-100% EtOAc/Hexane) to afford 55B (216 mg, 42%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.98 (t, 3 H) 2.42 (q, 2 H) 2.73 (t, 2 H) 4.10 (t, 2 H) 6.82 (d, 1 H) 7.02 (d, H) 7.09 (t, 2 H) 7.15 (t, 1 H) 7.36 (d, 1 H) 7.58-7.63 (m, 1 H).

1. customThe reaction was quenched with 1N NaOH (20 mL)
2. washwashed with EtOAc (20 mL)
3. extractionextracted with EtOAc (2×20 mL)
4. washThe combined organics were washed with brine (10 mL)
5. dry with materialdried (MgSO4)
6. concentrationThe organic layer was concentrated in vacuo
7. customthe residue purified by flash chromatography (0-100% EtOAc/Hexane)

ORD record

ord-e768230ac9a444d6b9ec18c387226f20

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592331B2