Methanol → 125604-03-7

HRID 45226Notes

Reaction equation

HRID 45226 reaction equation
Cl.C(N(C1C=CC=CC=1)S(C1C=NC(N2C(=O)C(CC3C=NC=CC=3)=C(C)N2)=CC=1)(=O)=O)C.[CH3:34][O:35][CH2:36][C:37]1[CH:38]=[C:39]([CH2:43]O)[CH:40]=[CH:41][CH:42]=1.P(Br)(Br)[Br:46].CO>CCOCC>[Br:46][CH2:43][C:39]1[CH:40]=[CH:41][CH:42]=[C:37]([CH2:36][O:35][CH3:34])[CH:38]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24614Phosphorus tribromideHCID 12067857[3-(Methoxymethyl)phenyl]methanolHCID 86659736N-ethyl-6-[3-methyl-5-oxo-4-(pyridin-3-ylmethyl)-2,5-dihydro-1H-pyrazol-1-yl]-N-phenylpyridine-3-sulfonamide hydrochloride

Product 1

HCID 57975474125604-03-7Yield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5.91 g (38.8 mmol) of 2 [3-(methoxymethyl)phenyl]methanol in 75 mL of Et2O are added dropwise, at 0° C., 9.1 mL (97.1 mmol) of phosphorus tribromide. The reaction mixture is allowed to warm slowly to room temperature and stirring is continued for 4 hours. The crude reaction mixture is then poured cautiously into a mixture of 100 g of ice and 100 mL of MeOH. After evaporating off the MeOH under reduced pressure, the aqueous phase is extracted with DCM (2×200 mL). The organic phases are combined, dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc. 3.25 g of 1-(bromomethyl)-3-(methoxymethyl)benzene are thus obtained in the form of an oil.

Workup

  1. customThe crude reaction mixture
  2. customAfter evaporating off the MeOH under reduced pressure
  3. extractionthe aqueous phase is extracted with DCM (2×200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica gel
  9. washeluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc

Sources & evidence

ORD record
ord-15c03bfb41a9418b8cefc422d01ada83
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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