Hydroquinone → Fluazifop-butyl

HRID 1648977

Reaction equation

HRID 1648977 reaction equation
[Na].[C:2]1([CH:9]=[CH:8][C:6]([OH:7])=[CH:5][CH:4]=1)[OH:3].Br[C:11](=[CH2:19])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13].C([O-])(=O)C=C.Cl[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=1>C(O)CCC>[F:33][C:32]([F:35])([F:34])[C:29]1[CH:30]=[CH:31][C:26]([O:3][C:2]2[CH:9]=[CH:8][C:6]([O:7][CH:11]([CH3:19])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])=[CH:5][CH:4]=2)=[N:27][CH:28]=1

Participants

7

Reactant 5

HCID 785HydroquinoneHCID 25188AcrylateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 5360545Sodium2×HCID 19901948HCID 19901948, compound

Product 1

HCID 50897Fluazifop-butyl

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Sodium (6.9 g, 0.3 mol) was added to n-butanol (200 ml) under nitrogen. When the sodium had reacted, the solution was cooled to room temperature and hydroquinone (16.5 g, 0.15 mol) was added. The temperature was raised to 45° and n-butyl 2-bromoacrylate (26 g, 0.125 mol) was added dropwise. When the acrylate had all been added, the mixture was stirred for 20 hours and then 2-chloro-5-trifluoromethylpyridine (27.2 g, 0.15 mol) was added. The resulting mixture was heated for 30 hours at 65°, allowed to cool, treated with carbon and filtered through Celite. The resulting solution was made up to 500 ml with n-butanol and a hydrogenation catalyst (10% palladium on carbon; 0.5 g) was added. The crude product was hydrogenated at ambient temperature and pressure until hydrogen uptake ceased to give n-butyl 2-[4-(5-trifluoromethylpyridin-2-yloxy)phenoxy]propionate.

Workup

  1. temperatureThe temperature was raised to 45°
  2. additionall been added
  3. temperatureThe resulting mixture was heated for 30 hours at 65°
  4. temperatureto cool
  5. additiontreated with carbon
  6. filtrationfiltered through Celite
  7. additiona hydrogenation catalyst (10% palladium on carbon; 0.5 g) was added
  8. customwas hydrogenated at ambient temperature

Sources & evidence

ORD record
ord-84acbdacc6cb4db8886cb215b4a0756b
Source dataset
uspto-grants-1983_11
Patent number
US04414391

Linked notes

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