Bromobenzene → (4-Bromophenyl)(4-fluorophenyl)methanone

Temperature

90 °C

4-Fluorobenzoyl chloride (238 g, 1.5 mol) is added under an atmosphere of nitrogen over a period of 1 hour to a suspension of anhydrous aluminium chloride (224 g, 1.68 mol) and 700 ml bromobenzene while maintaining the temperature below 30° C. After the addition is complete, the solution is heated at 90° C. for 3 hour. The reaction solution is added to 500 g crushed ice. The mixture is allowed to warm to room temperature and the water phase is extracted with dichloromethane (3 times with 200 ml). The organic extracts are combined, washed with water (200 ml), saturated sodium hydrogene carbonate solution (200 ml), water (200 ml), dried over sodium sulphate, filtered, and evaporated to dryness. The residue is crystallized twice from petroleum ether (b.p.: 36-80° C.) to obtain a pale yellow powder. The yield is 240-278 g (57-67%).

1. temperaturewhile maintaining the temperature below 30° C
2. additionAfter the addition
3. additionThe reaction solution is added to 500 g
4. customcrushed ice
5. temperatureto warm to room temperature
6. extractionthe water phase is extracted with dichloromethane (3 times with 200 ml)
7. washwashed with water (200 ml), saturated sodium hydrogene carbonate solution (200 ml), water (200 ml)
8. dry with materialdried over sodium sulphate
9. filtrationfiltered
10. customevaporated to dryness
11. customThe residue is crystallized twice from petroleum ether (b.p.: 36-80° C.)
12. customto obtain a pale yellow powder

ORD record

ord-47c6e53e8a614d32beceb47187ff349e

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459505B2