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

HRID 1642636Notes

Reaction equation

HRID 1642636 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 ambient temperature 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 2-benzyloxy-4-bromomethyl-1-nitrobenzene as a yellow solid.

Workup

  1. stirringby stirring at ambient temperature 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-53b32304d98e439d89260cd41c401ee4
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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