3-(Bromomethyl)isoquinoline synthesis
- Product Name:3-(Bromomethyl)isoquinoline
- CAS Number:54804-44-3
- Molecular formula:C10H8BrN
- Molecular Weight:222.08
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Yield:54804-44-3 71.7%
Reaction Conditions:
with 1H-imidazole;bromine;triphenylphosphine in dichloromethane at 0; for 0.166667 h;
Steps:
14.1 Step 1: Preparation of 3-(bromomethyl) isoquinoline
To a solution of 3-isoquinolylmethanol (400 mg, 2.51 mmol, 1 eq) and imidazole (188.18 mg, 2.76 mmol, 1.1 eq) in DCM (4 mL) was added PPh3 (308.12 mg, 2.76 mmol, 1.1 eq) and Br2 (723.12 mg, 1.17 mmol, 1.1 eq) at 0oC. The mixture was stirred at 0°C for 10 min. LC-MS showed Reactant 1 was consumed completely and one main peak with desired mass. The solvent was quenched by saturation sodium hydrogen sulfite (10 mL) and extracted with DCM 30 (3×10 mL). The organic layer was washed with brine (10 mL), dried by sodium sulfate and concentrated by reduced pressure to give residue. The residue was purified by prep-TLC (SiO2, PE: EA = 1:1). Compound 3-(bromomethyl) isoquinoline (400 mg, 1.801 mmol, 71.7% yield) was obtained as a white solid.
References:
WO2020/251957,2020,A1 Location in patent:Paragraph 00386-00387
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