Phosphorus tribromide → HCID 90460608, compound

HRID 588895Notes

Reaction equation

HRID 588895 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH2:13]O.[Br:15]P(Br)Br>ClCCl>[Br:15][CH2:13][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 117607196HCID 117607196, compound

Product 1

HCID 90460608HCID 90460608, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-chloro-4-methoxy-5-nitrophenyl)methanol (5.0 g, 23 mmol) in dichloromethane (50 mL) at 0° C., tribromophosphine (3.08 g, 11.5 mmol) was added in portions and the resulting mixture was stirred at RT for 2 h. The mixture was poured into ice-water and extracted with dichloromethane. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1) to afford the desired product (3.5 g, 54.2% yield).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-30511eff0ddb4324872315159000d2e3
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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