ChemicalBook CAS DataBase List 4-Cyano-2-fluorobenzyl alcohol

4-Cyano-2-fluorobenzyl alcohol synthesis

8synthesis methods

Product Name:4-Cyano-2-fluorobenzyl alcohol
CAS Number:219873-06-0
Molecular formula:C8H6FNO
Molecular Weight:151.14

4-Cyano-2-fluorobenzyl alcohol is an organic alcohol and can be used as an intermediate in organic synthesis. It can be obtained by the reaction of 2-fluoro-4bromobenzyl alcohol with zinc cyanide or by reduction of methyl 4-cyano-2-fluorobenzoate.

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219873-06-0
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Yield:219873-06-0 93%

Reaction Conditions:

with dimethylsulfide borane complex in tetrahydrofuran at 0 - 20; for 2 h;

Steps:

70.1
EXAMPLE 70; 5-Chloro-thiophene-2-carboxylic acid {3-[2-fluoro-4-(l-methyl-4,5-dihydro-lH-imidazol-2- yl)-phenyl] -isoxazol-5-ylmethyl} -amide; Step 1 :; [0580] Carboxylic acid 17 (20.18 g, 138 mmol) was diluted with 150 mL of THF and cooled to O0C. To this stirring solution was added BH3-S(CH3)2 complex (26 mL, 276 mmol) slowly which resulted in a vigorous reaction and significant gas evolution. The bath was removed and the reaction stirred at rt for 2 hrs at which time TLC and HPLC showed consumption of the starting material. The reaction was quenched by slow addition of water (vigorous exotherm), then the crude mixture was concentrated, diluted with ethyl acetate and filtered. The filtrate was concentrated to dryness affording the desired alcohol (18) as a white solid (17 g, 93%). NMR (DMSO-cfo 400 MHz): δ 7.76 (d, IH), δ 7.67 (m, 3H), δ 5.50 (t, IH), δ 4.55 (d, 2H).

References:

MILLENNIUM PHARMACEUTICALS, INC. WO2006/2099, 2006, A2 Location in patent:Page/Page column 103-104

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188582-62-9 Synthesis