Sulfuric Acid → HCID 12844397, compound

1,2-Bis(m-bromophenyl)ethane was prepared by the method of Lindsay et al (JACS, 1961, 83, 943) as follows. Magnesium (0.05 g, 2.0 mmol) was added to a solution of 3-bromobenzylbromide (1.0 g, 4.0 mmol) in Et2O (10 mL) at rt. After 20 min at room temperature all the magnesium had dissolved and anhydrous ferric chloride (5 mg) was added. The reaction was heated to reflux for 1 hour, cooled, acidified to about pH 1 with 1 M aqueous H2SO4 and extracted with Et2O (3×50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4), filtered and concentrated in vacuo to give a yellow solid. Recrystallization from petroleum ether gave 1,2-bis(m-bromophenyl)ethane as a colorless solid. MS (APCI) m/z 338 (50%), 340 (100), 342 (50). 1H NMR (200 MHz, CDCl3): δ2.85, s, 2H; 7.02-7.25, m, 2H; 7.30-7.39, m, 2H.

1. custom1,2-Bis(m-bromophenyl)ethane was prepared by the method of Lindsay et al (JACS, 1961, 83, 943)
2. temperatureThe reaction was heated
3. temperatureto reflux for 1 hour
4. temperaturecooled
5. extractionextracted with Et2O (3×50 mL)
6. washThe combined organic extracts were washed with water (50 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a yellow solid
11. customRecrystallization from petroleum ether

ORD record

ord-77a2a8bdfdf34edc9c77cbc5bd97d358

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06355683B1