ChemicalBook CAS DataBase List 5-Bromo-2-hydroxymethylpyridine

5-Bromo-2-hydroxymethylpyridine synthesis

13synthesis methods

Product Name:5-Bromo-2-hydroxymethylpyridine
CAS Number:88139-91-7
Molecular formula:C6H6BrNO
Molecular Weight:188.02

5-bromo-2-pyridinecarboxylic acid, methyl ester (648mg, 3mmol) in 10ml of methanol was slowly added to sodium borohydride (340mg, 9mmol) in an ice bath. After that, the ice bath was removed and the reaction mixture was warmed to room temperature. The reaction was stirred for 12 hours. Then 1N HCl was added to adjust the pH to 1. Afterward, a saturated sodium bicarbonate solution was added to adjust the pH to 8. The mixture was then extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. This resulted in the formation of 535mg of white solid, which was identified as 5-bromo-2-pyridinemethanol. The yield of the desired product was 94.8%.
2-Hydroxymethyl-5-bromopyridine

3430-13-5 Synthesis

3430-13-5
425 suppliers
$5.00/5g

88139-91-7
262 suppliers
$11.00/1g

Yield:88139-91-7 78%

Reaction Conditions:

Stage #1:5-bromo-2-methylpyridine with 3-chloro-benzenecarboperoxoic acid in dichloromethane for 2 h;
Stage #2: with sodium carbonate

Steps:

413.A
Part A: Compound 413 (3.5 g, 20.7 mmol) was dissolved in methylene chloride (100 ml) and m-CPBA (4.95 g, 28.9 mmol) was added. The reaction mixture was stirred for two hours and then quenched with saturated sodium carbonate and stirred overnight. The organic layer was dried over sodium sulfate and the concentrated to provide a yellow solid (3.8 g). The solid was placed under argon and trifluoroacetic anhydride (15 mL) was added slowly. The reaction was stirred for 30 minutes at room temperature and then refluxed for 30 minutes. The reaction was cooled to room temperature and quenched slowly with saturated sodium bicarbonate. Methylene chloride was added and the organic layer was washed dried over sodium sulfate and concentrated. Column chromatography (2 to 1 ethyl acetate/hexanes) provided the desired product (3.O g, 78%).¹H NMR (400 MHz, CDCI₃) δ 8.65 (d, 1H), 7.8 (m, 1H), 7.2 (d, 1H), 4.7 (s, 2H).

References:

SCHERING CORPORATION WO2007/84451, 2007, A1 Location in patent:Page/Page column 146

31181-90-5 Synthesis