ChemicalBook CAS DataBase List Benzonitrile, 2-fluoro-5-(hydroxymethyl)- (9CI)

Benzonitrile, 2-fluoro-5-(hydroxymethyl)- (9CI) synthesis

4synthesis methods

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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Benzonitrile, 2-fluoro-5-(hydroxymethyl)- (9CI)

227609-85-0
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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

218301-22-5 Synthesis