Phosphorus tribromide → 1-(Bromomethyl)-2,3,5-trichlorobenzene

HRID 2292451Notes

Reaction equation

HRID 2292451 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[CH2:14]O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[CH2:14][Br:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 41018Benzene, 1,2,5-trichloro-3-methoxy-

Product 1

HCID 197050451-(Bromomethyl)-2,3,5-trichlorobenzeneYield 276%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 7.6 grams (0.028 mole) of phosphorus tribromide in 200 mL of toluene was stirred, and 17.0 grams (0.080 mole) of 2,3,5-trichlorophenylmethanol was washed into the reaction vessel with about 5 mL of toluene. Upon completion of the addition the reaction mixture was stirred at ambient temperature for about 16 hours. The reaction mixture was then concentrated under reduced pressure to a residue. The residue was dissolved in ethyl acetate and washed with three portions of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 21.2 grams of 2,3,5-trichlorophenylmethyl bromide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. concentrationThe reaction mixture was then concentrated under reduced pressure to a residue
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with three portions of water
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-656dbd2dee9d4b3fa143e364d442840e
Source dataset
uspto-grants-1997_11
Patent number
US05683966

Reaction notes

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