Water → HCID 20380612, compound

HRID 1448642Notes

Reaction equation

HRID 1448642 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:9]([CH2:10]O)=[C:8]([CH3:17])[C:7]=1[N+:18]([O-:20])=[O:19].O>C1C=CC=CC=1>[Br:2][CH2:17][C:8]1[C:9]([CH3:10])=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:6]([Cl:5])[C:7]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 911839172908-02-2

Product 1

HCID 20380612HCID 20380612, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosphorus tribromide (18.0 g; 0.067 mol) is added dropwise at 10° C. to a stirred slurry of 4-chloro-2-methyl-3,5-dinitrobenzyl alcohol (50.0 g; 0.20 mol) in benzene (100 ml). The reaction mixture is allowed to warm to room temperature and then heated to reflux for 5 hours. After standing at room temperature overnight, the mixture is poured into water and extracted with ether. Insoluble material present is collected and dried to yield 18.9 g solid, melting point 115°-120° C. Removal of the ether from the extracts yields additional 38.6 g solid, melting point 106° C.-112° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. extractionextracted with ether
  4. customInsoluble material present is collected
  5. customdried

Sources & evidence

ORD record
ord-8d9b081bf1db4efcaa77c37baa903314
Source dataset
uspto-grants-1979_12
Patent number
US04180679

Reaction notes

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