Water → 2-Bromo-5-ethoxy-2',4'-difluorobiphenyl-4-carbaldehyde

HRID 531142Notes

Reaction equation

HRID 531142 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[CH:18]=[CH:19][C:20]=1[CH:21]=[O:22])[CH3:13].O>CN(C=O)C>[Br:1][C:18]1[CH:19]=[C:20]([CH:21]=[O:22])[C:15]([O:14][CH2:12][CH3:13])=[CH:16][C:17]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30]

Participants

5

Reactant 3

HCID 962WaterHCID 192912Dibromoisocyanuric acidHCID 117992075HCID 117992075, compound

Product 1

HCID 1179923172-Bromo-5-ethoxy-2',4'-difluorobiphenyl-4-carbaldehydeYield 148.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dibromoisocyanuric acid (3.39 g) was added to a solution of 3-ethoxy-2′,4′-difluorobiphenyl-4-carbaldehyde (5.16 g) in DMF (30 mL) at room temperature. The mixture was stirred at room temperature for 4 hours. Water (6 mL) was added to the mixture. Then the crystalline seed was added to the mixture. The mixture was stirred at room temperature for 1 hour. The precipitate was collected by filtration, washed with DMF-water (8 mL-2 mL), and dried at 70° C. to give the title compound (6.00 g).

Workup

  1. additionThen the crystalline seed was added to the mixture
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with DMF-water (8 mL-2 mL)
  5. customdried at 70° C.

Sources & evidence

ORD record
ord-3057342f5cf14b15a6f6099935e2b8ac
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

Loading…