Benzoyl Peroxide → HCID 14888669, compound

HRID 840135Notes

Reaction equation

HRID 840135 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:17])([F:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCCCCC>[Br:25][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:16])([F:17])[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 109991821,1-Dimethylethyl α,α-difluoro-4-methylbenzeneacetate

Product 1

HCID 14888669HCID 14888669, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To tert butyl 2-{4-(methyl)phenyl}-2,2-difluoroacetate(see X. Creary, J. Org. Chem. 1987, 52, 5026) (4.8 g) in CC14 (80 mL) was added NBS (3.8 g), followed by benzoyl peroxide (100 mg). The reaction mixture was heated at reflux and was irradiated with a sun lamp for 1.5 h. The mixture was cooled down and diluted with hexane (50 mL) purified by filtration on a pad of silica gel. The filtrate was concentrated to give the title product for step 2 as a yellow-brown liquid (6.4 g) 1H NMR δ: (CD3COCD3), 1.48 (9H, m), 4.70 (2H, s), 7.62 (4H, m).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. customwas irradiated with a sun lamp for 1.5 h
  4. temperatureThe mixture was cooled down
  5. filtrationpurified by filtration on a pad of silica gel
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2f45f678453e4d1a8f6932654b944206
Source dataset
uspto-grants-2002_04
Patent number
US06365592B1

Reaction notes

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