Carbon tetrabromide → 2-Bromomethyl-6-(1-methoxy-1-methylethyl)pyridine

HRID 876998Notes

Reaction equation

[C:1]([Br:5])(Br)(Br)Br.OC[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:17][CH3:18])([CH3:16])[CH3:15])[N:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:5][CH2:1][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:17][CH3:18])([CH3:15])[CH3:16])[N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Carbon tetrabromide (1.59 g, 4.80 mmol) was added portionwise to a stirred solution of 2-hydroxymethyl-6-(1-methoxy-1-methylethyl)pyridine (724 mg, 4.00 mmol) and triphenylphosphine (1.15 g, 4.40 mmol) in DCM (50 mL) at 0° C. The mixture was stirred at 0° C. for 1 h then concentrated in vacuo. The residue was purified by column chromatography (20:1 to 5:1 isohexane:EtOAc) to give the title compound (732 mg, 75%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.69-7.65 (1H, m), 7.46-7.43 (1H, m), 7.32-7.30 (1H, m), 4.55 (2H, s), 3.17 (3H, s), 1.55 (6H, s).

Workup

concentrationthen concentrated in vacuo
customThe residue was purified by column chromatography (20:1 to 5:1 isohexane:EtOAc)

Sources & evidence

ORD record: ord-b53d569a60a74a57814e2e10a84e3f61
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987279B2

Reaction notes

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