Phosphorus tribromide → HCID 68941966, compound

HRID 628634Notes

Reaction equation

HRID 628634 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-6ae8cc92e5fa494287f4a2ff2c5e6d19
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

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