Phosphorus tribromide → HCID 22466901, compound

HRID 593506Notes

Reaction equation

HRID 593506 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:7]([CH:10]=1)[C:8]#[N:9].P(Br)(Br)[Br:16]>C1(C)C=CC=CC=1.ClCCl>[Br:16][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 17966564HCID 17966564, compound

Product 1

HCID 22466901HCID 22466901, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A flask is charged with 5-hydroxymethyl-2-methylsulfonyl-benzonitrile (0.788 g, 3.73 mmol) in toluene (5 mL) and heated at 40° C. PBr3 (0.175 mL, 1.86 mmol) is added and the reaction is refluxed for 0.5 h. It is then cooled to room temperature, diluted with dichloromethane and washed with water. The aqueous layer is extracted with dichloromethane. The combined organic layer is dried over sodium sulfate and concentrated in vacuo to afford 5-bromomethyl-2-methanesulfonyl-benzonitrile as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.28 (s, 3H), 4.89 (s, 2H), 7.80 (d, J=8.3 Hz, 1H), 7.94 (s, 1H), 8.18 (d, J=8.1 Hz, 1H).

Workup

  1. temperaturethe reaction is refluxed for 0.5 h
  2. temperatureIt is then cooled to room temperature
  3. washwashed with water
  4. extractionThe aqueous layer is extracted with dichloromethane
  5. dry with materialThe combined organic layer is dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa66b07060d34a01b823cb596028a559
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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