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

HRID 415976Notes

Reaction equation

HRID 415976 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[CH2:11]O.P(Br)(Br)[Br:14].C([O-])(O)=O.[Na+]>C1COCC1>[Br:14][CH2:11][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[CH:5][C:4]=1[Cl:10]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 14484725(2,6-Dichloro-4-methoxyphenyl)methanol

Product 1

HCID 592994792-(Bromomethyl)-1,3-dichloro-5-methoxybenzeneYield 219.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (2,6-dichloro-4-methoxy-phenyl)-methanol (113 g, 545.76 mmol) in 1200 mL dry THF and cool to 0 deg under nitrogen. Add PBr3 (59.1 g, 218.3 mmol) under nitrogen and stir at 0° C. for 30 minutes. Pour into saturated aqueous NaHCO3 and extract with EtOAc. Dry and concentrate under vacuum to obtain 129.4 g product as an off-white solid. NMR (CDCl3) δ 6.88 (s, 2H), 4.73 (s, 2H), 3.79 (s, 3H).

Workup

  1. temperaturecool to 0 deg under nitrogen
  2. extractionextract with EtOAc
  3. customDry
  4. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-08da340904dc4d589d01a113f9a49af0
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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