Dimethylformamide → 2-Bromo-4'-fluoro-5-methoxybiphenyl-4-carbaldehyde

HRID 531048Notes

Reaction equation

HRID 531048 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.CN(C=O)C.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[C:26]([O:32][CH3:33])[CH:25]=2)=[CH:20][CH:19]=1>O>[Br:1][C:29]1[CH:28]=[C:27]([CH:30]=[O:31])[C:26]([O:32][CH3:33])=[CH:25][C:24]=1[C:21]1[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 225667274'-Fluoro-3-methoxy-[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 904235612-Bromo-4'-fluoro-5-methoxybiphenyl-4-carbaldehydeYield 180.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibromoisocyanuric acid (10.6 g) was added at 15° C. to 30° C. to a DMF (90 mL) solution of 4′-fluoro-3-methoxybiphenyl-4-carbaldehyde (16.0 g), and the mixture was stirred for 40 minutes. Then, water (30 mL) was added thereto, and the mixture was further stirred for 1 hour. The deposited solid was collected by filtration and washed with a mixed solution of DMF (15 mL) and water (15 mL) and water (30 mL) in this order to obtain the title compound (20.6 g).

Workup

  1. stirringthe mixture was further stirred for 1 hour
  2. filtrationThe deposited solid was collected by filtration
  3. washwashed with a mixed solution of DMF (15 mL) and water (15 mL) and water (30 mL) in this order

Sources & evidence

ORD record
ord-8b661be5d8f44d37bb8fe0c8b0d3bf69
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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