Benzyl Bromide → HCID 264618, compound

HRID 643938Notes

Reaction equation

HRID 643938 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.O>[CH2:20]([O:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][CH:12]=[O:13])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4089953N-(2-Hydroxy-5-nitrophenyl)formamide

Product 1

HCID 264618HCID 264618, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-hydroxy-5-nitrophenyl)-formamide (26 g, 0.143 mol) in DMF (180 mL) is added potassium carbonate (22 g, 0.159-mol), followed by benzyl bromide (27 g, 0.158 mol) at 60° C. The mixture is stirred for 1.25 h. The mixture is diluted with water. The precipitated solid is separated by filtration and washed with 1N HCl, water and hexanes, and air dried for 18 h to afford N-(2-benzyloxy-5-nitrophenyl)-formamide as a white solid: (M−H)−=271.1.

Workup

  1. customThe precipitated solid is separated by filtration
  2. washwashed with 1N HCl, water and hexanes, and air
  3. customdried for 18 h

Sources & evidence

ORD record
ord-22bc48c7d4954d79aff906e2545c1ad4
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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