Hydrochloric Acid → HCID 57445080, compound

Add ethylmagnesium bromide (3 N, 53.9 mL, 74.9 mmol) to a solution of 2-bromo-4-fluorobenzonitrile(15 g, 73.5 mmol) and tetraisopropoxytitanium (23 mL, 162 mmol) in ether (25 mL) at −70° C. under N2. After stirring at the temperature for 10 min, let it warm-up to RT and stir for one hour. Add boron trifluoride etherate (BF3OEt2) (16.8 mL, 147 mmol) to the solution slowly and stir for another hour. After adding 1 N HCl (200 mL) and ether (150 mL), separate the ether layer. Add 10% NaOH (150 mL) to the aqueous solution and extract it with ether. Separate the organic layer and dry over magnesium sulfate. Filter and concentrate in vacuo to give a residue. Purify the residue by column chromatography (diethylether) to give the title compound (7.5 g, 44%). MS (ES) m/z 230 [M+1]+.

1. stirringstir for one hour
2. customseparate the ether layer
3. additionAdd 10% NaOH (150 mL) to the aqueous solution
4. extractionextract it with ether
5. customSeparate the organic layer
6. dry with materialdry over magnesium sulfate
7. filtrationFilter
8. concentrationconcentrate in vacuo
9. customto give a residue
10. customPurify the residue by column chromatography (diethylether)

ORD record

ord-41778117b3e64adaa1658bb1b94f0554

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063035B2