Water → HCID 45119101, compound

Synthesised from commercially available 2,6-difluoro-3-methoxybenzenecarbonitrile. Boron tribromide solution (1.0 M in CH2Cl2, 118.3 ml, 118.3 mmol, 2 equiv.) was added slowly, dropwise to stirred solution of 2,6-difluoro-3-methoxybenzenecarbonitrile (10 g, 59.1 mmol, 1 equiv.) in CH2Cl2 (270 ml), at room temperature The reaction mixture was stirred at room temperature for 5 days. The reaction mixture was poured into water (600 ml), separated and extracted with CH2Cl2 (200 ml×2). The extracts were washed with water (250 ml×3) and dried (Na2SO4) to give a buff solid (7.15 g). This was dissolved in dichloromethane (250 ml) and extracted with dilute aqueous NaOH (6 g in 250 ml of water×2). The basic extracts were washed with CH2Cl2 (100 ml×3) and then acidified to pH 2 using concentrated HCl, extracted with CH2Cl2 (150 ml×4), washed with water (100 ml×2) and dried (Na2SO4) to give the desired compound as a cream solid (5.05 g). Yield 55%, mp 119-121° C., HPLC (Gemini C18, 50×4.6 mm): m/z 154 [M−H]−, Rt=3.07 min.

1. customseparated
2. extractionextracted with CH2Cl2 (200 ml×2)
3. washThe extracts were washed with water (250 ml×3)
4. dry with materialdried (Na2SO4)

ORD record

ord-aa9832451fb84742aa8e4cb1730dece9

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415383B2