Phosphorus tribromide → 4-(Bromomethyl)-1-methoxy-2-nitrobenzene

HRID 1776466Notes

Reaction equation

HRID 1776466 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].P(Br)(Br)[Br:15]>C(Cl)Cl.O.[Cl-].[Na+].O>[Br:15][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

6

Reactant 2

HCID 24614Phosphorus tribromideHCID 4432413(4-Methoxy-3-nitrophenyl)methanol

Product 1

HCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzeneYield 191.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

(4-methoxy-3-nitrophenyl)methanol (215 mg, 1.174 mmol) was dissolved, under N2 atmosphere, in dry DCM and cooled to 0° C. PBr3 (55.4 μl, 0.587 mmol) was added, and the reaction was stirred RT for 1 hour. Ice and DCM were added to the reaction mixture. The mixture was diluted with WATER and brine and extracted twice with DCM. The organic layers were dried and evaporated to dryness to give 4-(bromomethyl)-1-methoxy-2-nitrobenzene (276 mg, 1.122 mmol, 96% yield) that was used in the next step without further purification.

Workup

  1. extractionextracted twice with DCM
  2. customThe organic layers were dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-91fceaf44d2e4c51af25f445fe8b23c3
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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