Dimethylformamide → 6-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehyde

HRID 2272508Notes

Reaction equation

HRID 2272508 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.CN(C=O)C.[F:17][C:18]1[C:23]([OH:24])=[C:22]([CH:25]=[O:26])[CH:21]=[CH:20][C:19]=1[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1>O>[Br:1][C:20]1[C:19]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[C:18]([F:17])[C:23]([OH:24])=[C:22]([CH:25]=[O:26])[CH:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 904239512,4'-Difluoro-3-hydroxy-[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 904231046-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehydeYield 181.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibromoisocyanuric acid (8.87 g) was added at room temperature to a DMF (75 mL) solution of 2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (12.7 g), and the mixture was stirred at room temperature for 30 minutes. Water (50 mL) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. The resulting solid was collected by filtration, then washed with DMF-water, and dried to obtain the title compound (17.6 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with DMF-water
  4. customdried

Sources & evidence

ORD record
ord-8b6d88c2c2304973872962e6e7360369
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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