4-BROMO-3-HYDROXYMETHYL-BENZONITRILE synthesis
- Product Name:4-BROMO-3-HYDROXYMETHYL-BENZONITRILE
- CAS Number:905710-66-9
- Molecular formula:C8H6BrNO
- Molecular Weight:212.04
89003-95-2
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Yield: 90%
Reaction Conditions:
with methanol;sodium tetrahydroborate at 0; for 0.5 h;
Steps:
3 Example 3: Preparation of 4-bromo-3-(hydroxymethyl)benzonitrile (Compound C3)
To a solution of 4-bromo-3-formylbenzonitrile (1 g, 0.0047 mol) in methanol (10 mL) was added sodium borohydride(NaBH4; 0.18 g, 0.0047 mol) in portions, and the resulting mixture was stirred at 0 °C for 30 minutes (min). The reaction was quenched with saturated ammonium chloride (NH4C1) solution, and the mixture was concentrated under vacuum to remove the methanol. The resulting mass was dissolved in EtOAc, and the organic layer was washed with 0 and brine, dried over Na2S04 and concentrated. Trituration of the colorless solid which was obtained with n-hexane provided the title compound as white solid (0.9 g, 90%): mp: 131-133° C; NMR (400 MHz, CDCb) δ 7.86 (dt, J = 1.8, 0.9 Hz, 1H), 7.67 (d, / = 8.1 Hz, 1H), 7.45 (ddt, / = 8.2, 2.0, 0.7 Hz, 1H), 4.79 (s, 2H).
References:
DOW AGROSCIENCES LLC;BRAVO-ALTAMIRANO, Karla;CASTELLO, Olena;GRUBER, Joseph M.;MARKLEY, Lowell;RIAR, Dilpreet S.;ROTH, Joshua;YAP, Maurice C. WO2018/156554, 2018, A1 Location in patent:Page/Page column 25
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