Pyridine → 1-(Bromomethyl)-2-methoxy-3-nitrobenzene

HRID 618244Notes

Reaction equation

HRID 618244 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:12]O.N1C=CC=CC=1.P(Br)(Br)[Br:21]>ClCCl>[Br:21][CH2:12][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 18789679(2-Methoxy-3-nitrophenyl)methanol

Product 1

HCID 186220771-(Bromomethyl)-2-methoxy-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14.7 g of (2-methoxy-3-nitro-phenyl)-methanol dissolved in 140 ml of dichloromethane and 5.5 ml of pyridine was cooled in an ice bath and slowly added 6.48 ml of phosphorus tribromide. After 45 minutes at 5° C., the reaction mixture was diluted with dichloromethane, washed with water, dried, and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (5:95) giving 7.3 g of 1-bromomethyl-2-methoxy-3-nitrobenzene as a yellow solid. ##STR137##

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (5:95)

Sources & evidence

ORD record
ord-8c50ffb64fc943a28a3b698344fe465e
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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