N-bromobutanimide → 2-Bromo-1-(bromomethyl)-4-chlorobenzene

To a 500 ml 3-necked pyrex round bottomed flask equipped with a magnetic stirring bar, reflux condenser and argon inlet was added 2-bromo-4-chlorotoluene (10.00 g, 48.67 mmol), N-bromosuccinimide (18.66 g, 48.67 mmol) and dry, degassed carbon tetrachloride (200 ml). The stirred mixture was heated at reflux while being irradiated at a distance 10 cm by a 150 watt Hanovia low pressure mercury Lamp for 4 hours. The cooled reaction mixture was diluted with carbon tetrachloride and washed with water (2×200 ml) and brine (400 ml). Drying (MgSO4), filtration, and removal of the solvent in vacuo left compound (2a) as a colorless oil. HPLC analysis indicates the material to be approximately 80% of the monobromo and 20% of the dibromo material. 'H NMR (CDCl3) δ4.55 (s, 2H), 7.00-7.65 (m, 3H).

1. customTo a 500 ml 3-necked pyrex round bottomed flask equipped with a magnetic stirring bar
2. temperaturereflux condenser and argon inlet
3. customdry
4. customdegassed carbon tetrachloride (200 ml)
5. temperatureThe stirred mixture was heated
6. temperatureat reflux
7. customwhile being irradiated at a distance 10 cm by a 150 watt Hanovia low pressure mercury Lamp for 4 hours
8. customThe cooled reaction mixture
9. washwashed with water (2×200 ml) and brine (400 ml)
10. customDrying
11. filtration(MgSO4), filtration, and removal of the solvent in vacuo
12. waitleft compound (2a) as a colorless oil

ORD record

ord-7bc321117b9b405a9c04254012939238

Source dataset

uspto-grants-1986_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04593033