Water → HCID 21737106, compound

HRID 2400548Notes

Reaction equation

HRID 2400548 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=1.P(Br)(Br)[Br:18].O>ClCCl>[Br:18][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 20684020HCID 20684020, compound

Product 1

HCID 21737106HCID 21737106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[2-(2-methoxyethoxy)ethoxy]phenyl}methanol (Step 2, 500 mg, 2.21 mmol) in 10 mL dichloromethane was added dropwise phosphorous tribromide (210 μL, 2.21 mmol) at 0° C. After the addition was completed, stirring of the reaction mixture was continued for 1 h at the same temperature. Then, water was added with caution, and it was extracted with ethyl acetate. The combined organic layers were washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo to yield a crude product which was purified by MPLC (silica, cyclohexane/ethyl acetate 10:1) affording the title compound in pure form (530 mg, 83%): 1H NMR (400 MHz, CDCl3) δ 7.31 (d, 2H), 6.88 (d, 2H), 4.50 (s, 2H), 4.13 (t, 2H), 3.85 (t, 2H), 3.71 (t, 2H), 3.58 (t, 2H), 3.40 (s, 3H); DCI(NH3)-MS m/z 306/308 (M+NH4)+; HPLC RT (Method I) 3.20 min.

Workup

  1. additionAfter the addition
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customto yield a crude product which
  8. customwas purified by MPLC (silica, cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-a3dcb313f8b349a1acb217a3cf2c4d57
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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