Pyridine → HCID 67693831, compound

HRID 1648688Notes

Reaction equation

HRID 1648688 reaction equation
P(Br)(Br)[Br:2].N1C=CC=CC=1.[CH3:11][C:12]1([CH3:29])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16](/[C:24](/[CH3:28])=[CH:25]/[CH2:26]O)[CH:15]=[CH:14][C:13]1=2>C(OCC)C>[CH3:11][C:12]1([CH3:29])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16](/[C:24](/[CH3:28])=[CH:25]/[CH2:26][Br:2])[CH:15]=[CH:14][C:13]1=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 22091595HCID 22091595, compound

Product 1

HCID 67693831HCID 67693831, compoundYield 268.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of phosphorous tribromide (0.31 g, 1.16 mmol) and pyridine (0.057 g, 0.72 mmol) in petroleum ether (18 mL) was cooled to -10° C. under argon. The mixture was treated with a solution of 35 (0.94 g, 3.62 mmol) in anhydrous diethyl ether (18 mL). The reaction mixture was allowed to warm to room temperature over 2.5 h. The solution was then diluted with diethyl ether and washed twice with water. The aqueous layers were combined and back-extracted with another portion of diethyl ether. The organic layers were combined, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 1.00 g (86%) of 36 as an off-white solid. The bromide was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3) δ7.33 (d, 1H, ArH), 7.28 (d, 1H, ArH), 7.18 (dd, J=12 Hz, 1H, ArH), 6.05 (t, J=9 Hz, 1H, C=CH), 4.12 (d, J=9 Hz, 2H, CH2Br), 2.13 (s, 3H, CH=CCH3), 1.68 (s, 4H, CH2CH2), 1.26 (s, 6H, 2'CH3), and 1.24 (s, 6H, 2×CH3).

Workup

  1. washwashed twice with water
  2. extractionback-extracted with another portion of diethyl ether
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5852ad85ffb449f5bb49a80b6081ff08
Source dataset
uspto-grants-1995_07
Patent number
US05436369

Reaction notes

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