4-BROMO-1-FLUORO-2-(PHENYLMETHOXY)BENZENE

To a solution of the product of step a) (0.802 g, 4. 20 mmol) and benzyl bromide (0.755 ml, 6.30 mmol) in acetone (10 ml) was added potassium carbonate (1.16 g, 8.40 mmol) and the mixture was heated at reflux for 16 h at 60C. The solid was filtered off washing with acetone and the filtrate evaporated. The residue was purified by flash chromatography eluting with 0-20percent ETOAC/ISOHEXANE to leave 1.04 (88percent) of the title compound as an oil that crystallized after cooling: AH (400 MHz, CDCL3) 5.08 (2 H, s), 6. 98 (2 H, m), 7.13 (1 H, dd, J7. 4, 2. 2 Hz), 7.37 (5 H, m).Two reactions were carried out in parallel and combined for work-up. A mixture of 9 5-bromo-2-fluorophenol (1-1) (850 g, 4.5 mol), 10 benzyl bromide (837 g, 4.9 mol) and 11 potassium carbonate (923 g, 6.7 mol) in 12 ACN (5 L) was stirred at 20° C. for 12 h. The reactions were combined and concentrated, diluted with water (8 L), and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (3 L), dried over sodium sulfate and concentrated. The crude product was purified through a silica gel pad (eluted with 3:1 petroleum ether:EtOAc) to give the title intermediate (1.83 kg, 73percent yield) as a white 13 solid.

Molecular Weight:281.12
XLogP3:4.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:279.98991
Monoisotopic Mass:279.98991
Topological Polar Surface Area:9.2
Heavy Atom Count:16
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes