Carbon tetrabromide → 2-Bromo-6-(bromomethyl)pyridine

HRID 1042360Notes

Reaction equation

HRID 1042360 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[Br:6][C:7]1[N:12]=[C:11](CO)[CH:10]=[CH:9][CH:8]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClCCl>[Br:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH2:1][Br:5])[N:12]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 129547962-Bromo-6-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Carbon tetrabromide (12.90 g, 38.88 mmol) was added in four portions to a solution of (6-bromo-pyridin-2-yl)methanol (5.00 g, 29.91 mmol) and PPh3 (8.24 g, 31.40 mmol) in dichloromethane (50 ml) at 0° C. The resulting solution was stirred 2 hours at 0° C. Solvent was removed under reduced pressure. The title compound was obtained by column chromatography. Spectroscopic data: 1H NMR (300 MHz, Acetone-d6) δ 4.66 (s, 2H) 7.57-7.60 (m, 2H) 7.76 (t, J=7.42 Hz, 1H).

Workup

  1. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d4cbec3bbd7740849c6969d278c36e13
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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