m-Xylyl bromide → HCID 2991896, compound

HRID 1019165Notes

Reaction equation

HRID 1019165 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[OH-].[Na+].[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br>CN(C=O)C.O>[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 12099m-Xylyl bromideHCID 14798Sodium HydroxideHCID 178418385HCID 178418385, compound

Product 1

HCID 2991896HCID 2991896, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of benzotriazole (3 g) in DMF (38 mL) at r.t. was added a solution of 10N NaOH (2.75 mL). After stirring for 25 min., 3-methylbenzyl bromide (3.9 mL) was added. The mixture was further stirred for 30 min, diluted with H2O, and extracted with EtOAc. The EtOAc extract was washed with brine (2×), water, brine, and was then dried (MgSO4) and concentrated. The residue was stirred in diethyl ether/hexane to give the title compound as a white solid.

Workup

  1. stirringThe mixture was further stirred for 30 min
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with brine (2×), water, brine
  5. dry with materialwas then dried (MgSO4)
  6. concentrationconcentrated
  7. stirringThe residue was stirred in diethyl ether/hexane

Sources & evidence

ORD record
ord-abcc5ccbc24449198c7c5fadb7b6b773
Source dataset
uspto-grants-2002_11
Patent number
US06486142B2

Reaction notes

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