Phosphorus tribromide → 2-(Bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzene

HRID 1946298Notes

Reaction equation

HRID 1946298 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]=1[CH2:16]O.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:19][CH2:16][C:3]1[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 28945839{2-Chloro-6-[(phenylmethyl)oxy]phenyl}methanol

Product 1

HCID 595479962-(Bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of {2-chloro-6-[(phenylmethyl)oxy]phenyl}methanol (for a preparation see Intermediate 7) (1.1 g, 4.42 mmol) in DCM (12 ml) at 0-5° C. under nitrogen was added dropwise a solution of phosphorus tribromide (0.417 ml, 4.42 mmol, Aldrich) in DCM (3 ml). The solution was allowed to warm to ambient temperature and stirred for 3 h. The solution in an ice-water bath was diluted with dichloromethane (40 ml) and then treated with saturated aqueous sodium hydrogen carbonate (20 ml). The phases were separated and the organic extract dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as a yellow oil (0.829 g); LCMS: (System 1) (M-H)−=311, tRET=3.84 min.

Workup

  1. customat 0-5° C.
  2. customThe phases were separated
  3. extractionthe organic extract
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-692ba8351a2b4a9c87cfa0590f4beeb8
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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