Phosphorus tribromide → HCID 22466901, compound

HRID 1661552Notes

Reaction equation

HRID 1661552 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-e64852ceef484c9da8216e831f4300a7
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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