4-Fluorobenzoyl chloride → (4-Fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

HRID 432931Notes

Reaction equation

HRID 432931 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:9]=2[CH3:18])=[CH:5][CH:4]=1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:18][C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[C:13]([CH3:14])[C:8]=1[O:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:20]([C:26]([C:25]2[CH:29]=[CH:30][C:22]([F:21])=[CH:23][CH:24]=2)=[O:27])[CH:19]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 100846724-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Product 1

HCID 10046205(4-Fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanoneYield 53.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene (2.7 g, 10 mmol) and p-fluorobenzoyl chloride (4.0 g, 3.0 mL, 25 mmol) in methylene chloride (10 mL) was added titanium tetrachloride (1M in methylene chloride, 50 mL, 50 mmol). The reaction mixture was stirred at room temperature for 3 d, poured into ice (100 g), and stirred 1 h. The organic layer was separated and the aqueous layer was extracted with methylene chloride (3×50 mL). The combined organic extracts were washed with 5% sodium carbonate (200 mL), brine (150 mL), dried and concentrated. The residue was triturated with ether-petroleum ether. The solid was collected by filtration to give the title compound of Step A (2.1 g) as a tan solid. MS (APCl−Calc.: 395.2, Found: 394.2 (M−1).

Workup

  1. stirringstirred 1 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride (3×50 mL)
  4. washThe combined organic extracts were washed with 5% sodium carbonate (200 mL), brine (150 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was triturated with ether-petroleum ether
  8. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-9a1ba7343789476e8f187b3516ee3dc7
Source dataset
uspto-grants-2003_12
Patent number
US06664291B2

Reaction notes

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