2-Bromo-3-nitrotoluene → HCID 22493351, compound

HRID 1816282Notes

Reaction equation

HRID 1816282 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].C([Sn](CCCC)(CCCC)[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)CCC>>[CH3:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 2318282-Bromo-3-nitrotolueneHCID 27793732-(Tri-n-butylstannyl)thiophene

Product 1

HCID 22493351HCID 22493351, compoundYield 62%

Procedure

2-Bromo-3-nitrotoluene (3.35 g, 15.5 mmol) and 2-(tributylstannyl)-thiophene (5.7 g, 15.3 mmol, 1.0 eq) were coupled as in Example 75 to give 2.08 g of 2-(2-methyl-6-nitrophenyl)thiophene, which was reduced under conditions similar to Example 64 to give 1.4 g of 3-methyl-2-(2-thienyl)aniline.

Sources & evidence

ORD record
ord-437cfcee3f1145a5b118fd6bbe8920a2
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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