Trifluoroacetic acid → 3-(4-Bromophenethoxy)propanoic acid

tert-Butyl 3-[2-(4-bromophenyl)ethoxy]propanoate (Example 10a), 1.0 g) was dissolved in dichloromethane (10 mL) and treated with trifluoroacetic acid (2.5 mL). The mixture was stirred at room temperature for 3 hours, then concentrated in vacuo and azeotroped with dichloromethane (2×10 mL). The residue was taken up in dichlormethane (10 mL) and extracted with 1M sodium hydroxide (20 mL). The basic layer was washed with dichloromethane (20 mL) then acidified with 2M hydrochloric acid. The acidic layer was extracted with dichloromethane (2×20 mL). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated to yield the sub-titled compound (0.81 g) as an oil.

1. concentrationconcentrated in vacuo
2. customazeotroped with dichloromethane (2×10 mL)
3. extractionextracted with 1M sodium hydroxide (20 mL)
4. washThe basic layer was washed with dichloromethane (20 mL)
5. extractionThe acidic layer was extracted with dichloromethane (2×20 mL)
6. washwashed with brine
7. dry with materialdried over anhydrous magnesium sulphate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-59b6ceb15f334207ace7b83cf3b82435

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709511B2