1-Bromo-4-nitrobenzene → Nitrobenzene

HRID 366864Notes

Reaction equation

HRID 366864 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)C1SC=C(OCCCCCCCCCC)C=1OCCCCCCCCCC)CCC>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>[N+:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 114661-Bromo-4-nitrobenzeneHCID 23290213HCID 23290213, compound

Product 1

HCID 7416NitrobenzeneYield 57%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a refluxing solution of 1-bromo-4-nitrobenzene (0.80 g, 3.98 mmol) in tolulene (200 mL) was added tetrakis(triphenylphosphine)palladium(0) (75 mg). After 20 min, 2-(tributylstannyl)-3,4-didecyloxythiophene (2.87 g, 4.19 mmol) was added via a syringe. After complete addition, the mixture was refluxed for a total of 15 h. After cooling, the mixture was filtered and evaporated to afford a solid. Filtration using hot hexane gave 1-(3,4-didecyloxy)thien-2-yl)-4-nitrobenzene, recrystallized from ethanol containing 2% acetone, 1.17 g, yield=57%, mp=40-41.5° C. IR (KBr) 3127, 2919, 1594, 1512, 1464, 1339 and 848. 1H NMR (δ ppm): 0.880 (t, J=7.2 Hz, 6H), 1.411 (m, 28H), 1.769 (m, 4H), 3.986 (t, J=7.2 Hz, 2H), 4.092 (t, J=7.2 Hz, 2H), 6.263 (s, 1H), 7.903 (d, J=10.2 Hz, 2H) and 8.208 (d, J=10.2 Hz, 2H). 13C NMR (δ ppm): 14.26, 22.69, 29.34, 29.60, 30.12, 30.64, 30.73, 31.71, 31.91, 32.37, 70.18, 73.09, 97.19, 122.46, 123.94, 126.94, 140.16, 145.08, 145.94 and 150.98. MS(EI) m/z (rel int): 517 [(M)+, 42], 377 [(M+ --C10H20), 18], 359 [(M+ --C10H22O),5], 333 [(M+ --C11H20S), 3],237 [(M+ --C20H40), 55] and 190 [(M+ --C20H41NO2), 8]. Anal. Calcd for C30H47NO4S: C, 69.59; H, 9.15; N, 2.71; S, 6.19. Found: C, 69.61; H, 9.20; N, 2.63; S, 6.06.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture was refluxed for a total of 15 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customevaporated
  6. customto afford a solid
  7. filtrationFiltration

Sources & evidence

ORD record
ord-379a77a91edc4a91a91621e1279de8f9
Source dataset
uspto-grants-2000_10
Patent number
US06130339

Reaction notes

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