Phosphorus tribromide → HCID 68941966, compound

HRID 1967696Notes

Reaction equation

HRID 1967696 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH3:14])[C:5]=1[CH2:6]O)[CH3:2].P(Br)(Br)[Br:16]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH3:14])[C:5]=1[CH2:6][Br:16])[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 43777052,6-DIETHOXYBENZYL ALCOHOL

Product 1

HCID 68941966HCID 68941966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of 2,6-diethoxybenzyl alcohol (1.0 g, 5.2 mmol) in THF (10 mL) was added phosphorous tribromide (0.48 mL, 5.1 mmol) dropwise. The reaction was allowed to warm to room temperature and stirred for 1 h. After quenching the reaction with water, the mixture was extracted with EtOAc. The combined organics were washed with brine and dried over Na2SO4. The solution was concentrated under reduced pressure to give 2,6-diethoxybenzyl bromide as a brown oil. Yield (1.3 g, 98%).

Workup

  1. customAfter quenching
  2. customthe reaction with water
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b656e8b285945f1be85b1fd47aa8e88
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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