Benzonitrile, 2-fluoro-5-(hydroxymethyl)- (9CI) synthesis
- Product Name:Benzonitrile, 2-fluoro-5-(hydroxymethyl)- (9CI)
- CAS Number:227609-85-0
- Molecular formula:C8H6FNO
- Molecular Weight:151.14
171050-06-9
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Yield: 350 mg
Reaction Conditions:
Stage #1:3-cyano-4-fluorobenzoic acid with 1,1'-carbonyldiimidazole in tetrahydrofuran at 0 - 20; for 0.5 h;
Stage #2: with sodium tetrahydroborate in tetrahydrofuran at 0 - 20; for 16 h;
Steps:
D51 2-fluoro-5-(hydroxymethyl)benzonitrile
D51 2-fluoro-5-(hydroxymethyl)benzonitrile To a solution of 3-cyano-4-fluorobenzoic acid (1.00 g, 6.06 mmol) in tetrahydrofuran (THF) (20 mL) was added dropwise CDI (1.47 g, 9.08 mmol) at 0 °C. After the reaction mixture was left at room temperature for 30 min, sodium borohydride (0.687 g, 18.2 mmol) was added dropwise at 0 °C. The reaction mixture was stirred at room temperature for 16 h, quenched with saturated aqueous NH4C1 and extracted with ethyl acetate. The organic part was separated, dried over Na2S04, filtered and concentrated. Purification via flash column (petroleum ether/ethyl acetate = 10/1) afforded the title product (350 mg). LC-MS (ESI): m/z 152 [M + H]+; 0.52 min (ret time).
References:
GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED;SANG, Yingxia;WAN, Zehong;ZHANG, Qing WO2014/114694, 2014, A1 Location in patent:Page/Page column 40-41
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