Phosphorus tribromide → HCID 86680625, compound

HRID 1497455Notes

Reaction equation

HRID 1497455 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([CH:16](O)[CH3:17])=[N:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Br)(Br)[Br:20]>C(Cl)(Cl)Cl>[Br:20][CH:16]([C:13]1[CH:12]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:15][N:14]=1)[CH3:17]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 86680624HCID 86680624, compound

Product 1

HCID 86680625HCID 86680625, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-(5-(4-nitrophenyl)pyridin-2-yl)ethanol (95 mg, 0.3 mmol) in chloroform (3 mL) was added PBr3 (0.1 mL, 1.1 mmol) at 0° C. and the reaction was stirred at 0° C. for about 3 h. The reaction mixture was quenched with saturated NaHCO3 solution (10 mL) and extracted with DCM (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude 2-(1-bromoethyl)-5-(4-nitrophenyl)pyridine as off brown liquid (95 mg, 79% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.98 (d, 1H), 8.31 (d, 2H), 8.22 (dd, 1H), 8.01 (d, 2H), 7.70 (d, 1H), 5.55 (dd, 1H), 2.04 (d, 3H), LC-MS m/z calcd for [M+H]+ 309.00. found 309.3.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution (10 mL)
  2. extractionextracted with DCM (2×100 mL)
  3. washThe combined organic extracts were washed with brine solution (10 mL), organic layer
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5e318de11e8d46dc8835d07d58a9c96f
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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