Carbon tetrabromide → 3-Bromo-5-(bromomethyl)pyridine

HRID 656510Notes

Reaction equation

HRID 656510 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Br:30])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 149329483-Bromo-5-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5-bromopyridin-3-yl)methanol (475 mg, 2.5 mmol) and triphenylphosphine (1.3 g, 5 mmol) were combined in methylene chloride (20 mL) and cooled to 0° C. carbon tetrabromide (927 mg, 2.8 mmol) was introduced in portions and the reaction was maintained at 0° C. for 1 h. The reaction was concentrated and purified by column chromatography on silica gel (0 to 50% ethyl acetate/hexanes) to produce 254 mg (41%) as a white solid. 1H-NMR (D6DMSO, 400 MHz) δ 8.65 (s, br, 2H), 8.18 (s, 1H), 4.73 (s, 2H). Mass spec.: 249.89 (MH)+.

Workup

  1. additionwas introduced in portions
  2. concentrationThe reaction was concentrated
  3. custompurified by column chromatography on silica gel (0 to 50% ethyl acetate/hexanes)
  4. customto produce 254 mg (41%) as a white solid

Sources & evidence

ORD record
ord-38fdae6145ca4fc8832b970b235ba9f7
Source dataset
uspto-grants-2011_12
Patent number
US08071778B2

Reaction notes

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