Veratryl alcohol → 3,4-Dimethoxybenzyl bromide

HRID 1434857Notes

Reaction equation

HRID 1434857 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]O.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][Br:14]

Participants

5

Reactant 3

HCID 7118Veratryl alcoholHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 109004583,4-Dimethoxybenzyl bromideYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 3,4-dimethoxybenzyl alcohol (10 g, 59.5 mmol), carbon tetrabromide (22 g, 65.4 mmol), and THF (250 mL) was added triphenylphosphine (17 g, 65.4 mmol) in THF (75 mL). The reaction was heated at 60° C. for 1 h and concentrated to an oil. To the residue was added 1:1 CH2Cl2:Et2O and the resulting solid was filtered. The filtrate was concentrated and chromatographed on florisil with CH2Cl2 to give the title compound (8.05 g, 59%).

Workup

  1. concentrationconcentrated to an oil
  2. additionTo the residue was added 1:1 CH2Cl2
  3. filtrationEt2O and the resulting solid was filtered
  4. concentrationThe filtrate was concentrated
  5. customchromatographed on florisil with CH2Cl2

Sources & evidence

ORD record
ord-bedb93fb3807413c9d537b12aac80018
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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