Water → HCID 61147515, compound

HRID 594198Notes

Reaction equation

HRID 594198 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:17]1[N:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1.O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[N:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 8471TriethylamineHCID 825442-Chloro-5-nitropyrimidine

Product 1

HCID 61147515HCID 61147515, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromophenol (200 mg) in tetrahydrofuran were added triethylamine (193 μL) and 2-chloro-5-nitropyrimidine (204 mg). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was added to water (20 mL) and extracted with ethyl acetate (20 mL). The obtained organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give the titled compound (294 mg) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate (20 mL)
  2. washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2343eb62368941c7bdaa3e59a8c7fab2
Source dataset
uspto-grants-2016_01
Patent number
US09242977B2

Reaction notes

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