Benzyl Bromide → HCID 15054011, compound

HRID 660815Notes

Reaction equation

HRID 660815 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:15]([O:14][C:5]1[CH:6]=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 140916902-Nitro-5-(trifluoromethyl)phenol

Product 1

HCID 15054011HCID 15054011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-nitro-5-trifluoromethylphenol (730 mg, 3.5 mmol), benzyl bromide (0.42 mL, 3.5 mmol), and potassium carbonate (200 mg) in DMF (10 mL) is stirred at RT for 48 h. The mixture is partitioned between water and EtOAc, the organic layer is concentrated and the residue is chromatographed using a gradient of 5-20% EtOAc/hexane as eluent to afford the title compound as a light yellow solid.

Workup

  1. customThe mixture is partitioned between water and EtOAc
  2. concentrationthe organic layer is concentrated
  3. customthe residue is chromatographed

Sources & evidence

ORD record
ord-a146db547eae4438803bf22d2e905393
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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