Sodium Carbonate → 1-Bromo-2-(bromomethyl)-3,5-dichlorobenzene

HRID 2356654Notes

Reaction equation

HRID 2356654 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10]O.P(Br)(Br)[Br:13].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10][Br:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 14153164(2-Bromo-4,6-dichlorophenyl)methanol

Product 1

HCID 104260681-Bromo-2-(bromomethyl)-3,5-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.1 g of the benzyl alcohol 35.4 were dissolved in 40 ml of dry dichloromethane and admixed dropwise at 5° C. with a solution of 0.455 ml of phosphorus tribromide in 10 ml of dichloromethane. The reaction mixture was stirred overnight and then neutralized with 5 ml of a saturated aqueous sodium carbonate solution. The organic phase was removed, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with n-heptane as the eluent. 2-Bromo-4,6-dichlorobenzyl bromide 35.3 was obtained.

Workup

  1. customThe organic phase was removed
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel with n-heptane as the eluent

Sources & evidence

ORD record
ord-6e293970af944d609abb954eacd082e2
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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