Toluene → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-bromo-3-trifluoromethyl-5-methoxypyridine

HRID 1835421Notes

Reaction equation

HRID 1835421 reaction equation
[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[C:20]([CH3:28])[C:4]=1[C:5]([C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][N+:10]([O-])=[CH:9][C:8]=1[O:18][CH3:19])=[O:6].C1(C)C=CC=CC=1.P(Br)(Br)([Br:38])=O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[C:20]([CH3:28])[C:4]=1[C:5]([C:7]1[C:8]([O:18][CH3:19])=[CH:9][N:10]=[C:11]([Br:38])[C:12]=1[C:13]([F:16])([F:15])[F:14])=[O:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24613Phosphorus oxybromideHCID 121513054-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide

Product 1

HCID 235036044-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-bromo-3-trifluoromethyl-5-methoxypyridineYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 7.2 g (18 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide, 7 ml of toluene, 17 ml of dimethylformamide and 10 g (35 mmol) of phosphorus oxybromide, 4.1 g (yield 49%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-bromo-3-trifluoromethyl-5-methoxypyridine (compound No. 124; m.p. 145-147° C.) was obtained in the same process as in Synthesis Example 9 step (f).

Sources & evidence

ORD record
ord-594cda97293a452996ccf596eaa16bb5
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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