Hydrogen Bromide → HCID 178419456, compound

HRID 2362400Notes

Reaction equation

HRID 2362400 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.Br.[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C>[Br-:1].[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][PH:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11776TriphenylphosphineHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 178419456HCID 178419456, compoundYield 183.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (5-bromopyridin-3-yl)methanol (1 g, 5.32 mmol) in acetic acid (Volume: 2 mL) was added hydrogen bromide (1.324 mL, 11.70 mmol) and triphenylphosphine (1.726 g, 6.38 mmol) then heat to 90° C. for four days, cooled to ambient temperature. The reaction mixture was wash with ether (20 mL×2) and EtOAc (20 mL×2) then was filtered and concentrated under high vacuum to remove solvent and provide a white solid of 3-bromo-5-((tri-phenylphosphino)methyl)pyridine bromide salt (3.05 g, 4.89 mmol, 92% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.64 (s, 1H), 8.24 (s, 1H), 7.94 (t, J=7.0 Hz, 3H), 7.83-7.70 (m, 12H), 7.46 (d, J=1.5 Hz, 1H), 5.32 (d, J=15.6 Hz, 2H), Mass spec.: 434.2 (MH)+.

Workup

  1. temperaturecooled to ambient temperature
  2. washThe reaction mixture was wash with ether (20 mL×2) and EtOAc (20 mL×2)
  3. filtrationthen was filtered
  4. concentrationconcentrated under high vacuum
  5. customto remove solvent

Sources & evidence

ORD record
ord-0ec9a226ed73460783e5356964615683
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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