Anisole → HCID 19354606, compound

HRID 377568Notes

Reaction equation

HRID 377568 reaction equation
[Br-].[Br-].[Br-].[Al+3].[F:5][CH:6]([F:33])[C:7]1[O:12][CH2:11][N:10]([C:13]([CH3:25])([CH3:24])[C:14]([O:16]CC2C=CC=CC=2)=[O:15])[C:9](=[O:26])[C:8]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(OC)C=CC=CC=1>[N+](C)([O-])=O.ClCCl>[F:33][CH:6]([F:5])[C:7]1[O:12][CH2:11][N:10]([C:13]([CH3:25])([CH3:24])[C:14]([OH:16])=[O:15])[C:9](=[O:26])[C:8]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7519AnisoleHCID 166749BromhydrolHCID 19354661HCID 19354661, compound

Product 1

HCID 19354606HCID 19354606, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6375NitromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of aluminium tribromide (3.85 g) in nitromethane was added in portions to a stirred solution of benzyl 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (1.93 g) and anisole (3.1 g) in dichloromethane at 0° C. under an inert atmosphere. The reaction mixture was stirred at 0° C. for 10 minutes and at ambient temperature for 2 hours and diluted with dichloromethane. The dichloromethane solution was washed in turn with 2 M hydrochloric acid and with water. The organic solution was extracted with 1 M sodium bicarbonate, the aqueous extract was then washed with diethyl ether and acidified to pH 1 with 2 M hydrochloric acid. The acidic solution was extracted with ethyl acetate, the extract was dried (magnesium sulphate) and evaporated under reduced pressure to give 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1, 3-oxazin-3-yl)-2-methylpropanoic acid (0.70 g) as a pink solid, m.p. 149-151° C.

Workup

  1. washThe dichloromethane solution was washed in turn with 2 M hydrochloric acid and with water
  2. extractionThe organic solution was extracted with 1 M sodium bicarbonate
  3. extractionthe aqueous extract
  4. washwas then washed with diethyl ether
  5. extractionThe acidic solution was extracted with ethyl acetate
  6. dry with materialthe extract was dried (magnesium sulphate)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4439e9df8bc44f02aa72e5f097c5a2f2
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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