Water → 2-Bromo-6-(methoxymethyl)pyridine

Temperature

2.5 °C

Add dropwise a solution of (6-bromo-pyridin-2-yl)-methanol (9.6; g, 51; mmol) in anhydrous tetrahydrofuran (29; mL) to a stirring suspension of sodium hydride (60% dispersion in oil, 2.45; g, 61; mmol) in anhydrous tetrahydrofuran (96; mL) cooled to 0-5° C. under nitrogen. After gas evolution ceases, add dropwise methyl iodide (10.9; mL, 77; mmol) and warm to room temperature over 1; hour. Add iced water (100; mL), dilute with brine (100; mL) and ethyl acetate (200; mL). Separate the layers. Extract the organic layer once with brine (100; mL), dry over sodium sulfate and decant the liquid. Concentrate to a pale yellow oil (11.1; g) and distill using a Kügelrohr apparatus to give the title product as a colorless liquid (10.1; g, b.p.=140-150° C. at 2.4; mbar, 93%). MS (m/z): 202, 204; (M+1).

1. temperaturewarm to room temperature over 1
2. customSeparate the layers
3. extractionExtract the organic layer once with brine (100; mL)
4. dry with materialdry over sodium sulfate
5. customdecant the liquid
6. concentrationConcentrate to a pale yellow oil (11.1; g)
7. distillationdistill

ORD record

ord-042b2498617c4391aeb0ef90a7d40eb8

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932274B2