Chloroform → Methyl 4-(2-bromoethyl)benzoate

A solution of thionyl chloride (4.8 g) in chloroform (10 ml) was added, dropwise, to a solution of 4-(2-bromoethyl)benzoic acid (5.7 g) in chloroform (40 ml) and anhydrous dioxan (20 ml). When the addition was complete, the mixture was heated under reflux for 2 hours then cooled to room temperature and further thionyl chloride (2.4 g) in chloroform (10 ml) was added. The mixture was heated under reflux for 2 hours then allowed to cool to room temperature and concentrated in vacuo to give an oil which was dissolved in methanol (50 ml) and heated under reflux for 10 minutes. On cooling to room temperature, the mixture was stirred for 48 hours then concentrated in vacuo. The residue was parititoned between ethyl acetate (200 ml) and 5% aqueous sodium carbonate (200 ml), the layers were separated and the organic layer was washed with water (150 ml) then dried (MgSO4) and concentrated in vacuo to give the title compound as an oil, yield, 5.7 g.

1. additionWhen the addition
2. temperaturethe mixture was heated
3. temperatureunder reflux for 2 hours
4. temperatureThe mixture was heated
5. temperatureunder reflux for 2 hours
6. temperatureto cool to room temperature
7. concentrationconcentrated in vacuo
8. customto give an oil which
9. temperatureheated
10. temperatureunder reflux for 10 minutes
11. temperatureOn cooling to room temperature
12. concentrationthen concentrated in vacuo
13. customthe layers were separated
14. washthe organic layer was washed with water (150 ml)
15. dry with materialthen dried (MgSO4)
16. concentrationconcentrated in vacuo

ORD record

ord-55e728921ff74a28a12b3f714740ecf0

Source dataset

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05340831