3-(6-BroMopyridin-3-yl)acrylic acid synthesis
- Product Name:3-(6-BroMopyridin-3-yl)acrylic acid
- CAS Number:1035123-89-7
- Molecular formula:C8H6BrNO2
- Molecular Weight:228.04
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Yield:1035123-89-7 88%
Reaction Conditions:
Stage #1: 3-(6-bromo-pyridin-3-yl)-acrylic acid methyl esterwith lithium hydroxide;water in tetrahydrofuran at 20; for 3 h;
Stage #2: with hydrogenchloride;water pH=5 - ~ 7;
Steps:
15.2
Step 2: 3-(6-Bromo-pyridin-3-yl)-acrylic acid To 3-(6-Bromo-pyridin-3-yl)-acrylic acid methyl ester (120 mg, 0.495 mmol) in THF was added a solution of 0.5 N-LiOH (2 eq) and the mixture was stirred for 3 hrs at room temperature. The resulting residue was dissolved in H2O, then washed three times with Et2O, and neutralized with 1N HCl to pH 5~7. The resulting solid filtered and washed with H2O and then dried in vacuo to give 3-(6-Bromo-pyridin-3-yl)-acrylic acid (100 mg, 88 %). 1H NMR (300 MHz, DMSO-d6): δ 8.67 (d, 1H, J=2.1 Hz), 8.11 (dd, 1H, J=8.4, 2.1 Hz), 7.69 (d, 1H, J=8.4 Hz), 7.59 (d, 1H, J=15.9 Hz), 6.71 (d, 1H, J=15.9 Hz).
References:
EP1882687,2008,A1 Location in patent:Page/Page column 27