Sodium Nitrite → HCID 89739001, compound

HRID 2278400Notes

Reaction equation

HRID 2278400 reaction equation
[N:1]([O-:3])=[O:2].[Na+].C(C1C(N)=C(C)C([N+]([O-])=O)=CC=1)C.[Br:18][C:19]1[C:24]([CH3:25])=[C:23]([N+]([O-])=O)[CH:22]=[CH:21][C:20]=1[CH2:29][CH3:30]>O.Br>[Br:18][C:19]1[C:20]([CH2:29][CH3:30])=[C:21]([N+:1]([O-:3])=[O:2])[CH:22]=[CH:23][C:24]=1[CH3:25]

Participants

6

Reactant 3

HCID 23668193Sodium NitriteHCID 89739126HCID 89739126, compoundHCID 89739707HCID 89739707, compound

Product 1

HCID 89739001HCID 89739001, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

NaNO2 (7.7 g, 110 mmol) in 15 mL of water was added slowly to a stirred solution of the products of Step 1 (19 g, 106 mmol) in 48% aqueous HBr (35 mL) at 0° C. CuBr (1.4 g, 10 mmol) in 48% aqueous HBr (10 mL) was added dropwise. After stirring for 15 mins, the mixture was heated at 90° C. for 2 hrs. After cooling, the mixture was diluted with water and extracted 5 times with EtOAc. The combined organic phases were concentrated and purified by silica gel column chromatography (PE/EtOAc=50:1) to yield a mixture of 2-bromo-1-ethyl-3-methyl-4-nitro-benzene and 2-bromo-3-ethyl-1-methyl-4-nitro-benzene (23 g, yield 95%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted 5 times with EtOAc
  3. concentrationThe combined organic phases were concentrated
  4. custompurified by silica gel column chromatography (PE/EtOAc=50:1)
  5. customto yield

Sources & evidence

ORD record
ord-7bac48adec544912bdcf4e03302d7657
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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