Phosphorus tribromide → 4-(BroMoMethyl)-1-chloro-2-nitrobenzene

HRID 923440Notes

Reaction equation

HRID 923440 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].P(Br)(Br)[Br:14]>C1(C)C=CC=CC=1>[Br:14][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 919334-Chloro-3-nitrobenzyl alcohol

Product 1

HCID 126237744-(BroMoMethyl)-1-chloro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (4-chloro-3-nitrophenyl)methanol (5.0 g, 26.6 mmol) in toluene (100 mL) was added phosphorus tribromide (0.879 mL, 9.32 mmol) at 40° C. The reaction mixture was stirred at 100° C. for 15 mins and partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28f38a5e97444b8eb5b8500c1ddbf2d1
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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