4-Bromo-1-(bromomethyl)-2-chlorobenzene → 6-[2-(4-Bromo-2-chloro-phenyl)-acetyl]-7-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one

HRID 2386826Notes

Reaction equation

HRID 2386826 reaction equation
[F:1][C:2]1[C:13]([C:14]([OH:16])=O)=[CH:12][C:5]2[N:6]([CH3:11])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.CN1C2C=CC(C(Cl)=O)=CC=2OC1=O.[Br:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[C:34]([Cl:40])[CH:33]=1>[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:14]([C:13]2[C:2]([F:1])=[CH:3][C:4]3[O:9][CH2:8][C:7](=[O:10])[N:6]([CH3:11])[C:5]=3[CH:12]=2)=[O:16])=[C:34]([Cl:40])[CH:33]=1

Participants

6

Reactant 3

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneHCID 666972667-fluoro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acidHCID 866458793-Methyl-2-oxo-2,3-dihydro-benzooxazole-6-carbonyl chloride

Product 1

HCID 666974056-[2-(4-Bromo-2-chloro-phenyl)-acetyl]-7-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

In analogy to Example 49, step 1, 7-fluoro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid was converted to the acid chloride and subsequently reacted with 4-bromo-1-bromomethyl-2-chloro-benzene in the presence of zinc and tetrakis(triphenylphosphine)palladium(0) to give the title compound as an off-white solid. MS (m/e)=412.2 [M+H+].

Sources & evidence

ORD record
ord-1e83d43de990493da5bb8f5faeb21831
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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