Triethylamine → 2-Benzyloxy-4-bromomethyl-1-nitrobenzene

HRID 660548Notes

Reaction equation

HRID 660548 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:18]O)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[Br-:32].[Li+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:18][Br:32])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 545187813-Benzyloxy-4-nitro-benzyl alcohol

Product 1

HCID 621150422-Benzyloxy-4-bromomethyl-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of (3-benzyloxy-4-nitrophenyl)-methanol (11.0 g, 0.042 mol) in anhydrous THF is added triethylamine (8.7 g, 0.86 mol). The mixture is cooled to −20° C., followed by the addition of methanesulfonyl chloride (5.8 g, 0.051 mol) and then stirred at −20° C. for 45 min. To this mixture is added lithium bromide (37.3 g, 0.43 mol) in anhydrous THF (40 mL) over 40 min followed by stirring at RT for 2 h. The suspension is concentrated under reduced pressure and diluted with EtOAc and water. The organic phase is washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound as a yellow solid.

Workup

  1. stirringby stirring at RT for 2 h
  2. concentrationThe suspension is concentrated under reduced pressure
  3. additiondiluted with EtOAc and water
  4. washThe organic phase is washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1a7f92c3d6bc4c7fb47a9954d733161e
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…