Phosphorus tribromide → 2-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene

HRID 2427465Notes

Reaction equation

HRID 2427465 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[CH2:17]O.P(Br)(Br)[Br:20].C([O-])(O)=O.[Na+]>C1COCC1>[Br:20][CH2:17][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:4]=1[Cl:16]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 66621751(4-Benzyloxy-2,6-dichloro-phenyl)methanol

Product 1

HCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzeneYield 222.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Treat a 0° C. solution of (2,6-dichloro-4-benzyloxy-phenyl)-methanol (247 g, 0.872 mol) in THF (2.5 L) with phosphorous tribromide (94.45 g, 0.35 mol) and stir for 30 minutes at 0° C. under N2. Pour the reaction into saturated NaHCO3 and extract twice with ethyl acetate. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford 269 g (89%) of the titled product. ES MS (m/z): 346 (M+1).

Workup

  1. additionPour
  2. extractionextract twice with ethyl acetate
  3. dry with materialDry the organic layer with Na2SO4
  4. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-64f1d5381b1b446c9b7520322048f142
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Reaction notes

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