Water → HCID 58027315, compound

HRID 643919Notes

Reaction equation

HRID 643919 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[C:5]([CH:11]=[CH2:12])[CH:4]=1.P(Br)(Br)[Br:14].O>C(OCC)C>[Br:14][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 66750906HCID 66750906, compound

Product 1

HCID 58027315HCID 58027315, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (4-methoxy-2-vinylphenyl)-methanol (7.90 g, 48.2 mmol) in diethyl ether (100 mL) at 0° C. is added PBr3 (5.0 mL, 53 mmol) over 1 min. Water is added carefully to destroy excess PBr3. The mixture is partitioned carefully between EtOAc and NaHCO3 (plus a small amount of KOH to adjust pH to 7˜8). The organic extract is dried with MgSO4 and concentrated to give the title compound and it is used directly in the next step: 1H NMR (CDCl3) δ 3.83 (s, 3H), 4.57 (s, 2H), 5.44 (dd, J=1, 11 Hz, 1H), 5.74 (dd, J=1, 17 Hz, 1H), 6.81 (dd, J=3, 8 Hz, 1H), 7.03 (d, J=2 Hz, 1H), 7.06 (dd, J=11, 17 Hz, 1H), 7.25 (d, J=8 Hz, 1H).

Workup

  1. customto destroy excess PBr3
  2. customThe mixture is partitioned carefully between EtOAc and NaHCO3 (plus a small amount of KOH
  3. extractionThe organic extract
  4. dry with materialis dried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2c2c064608342cab38b13019c32f8bd
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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