Water → 2-Methoxy-4-nitro-1,1'-biphenyl

HRID 1602787Notes

Reaction equation

HRID 1602787 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]([O:17][CH3:18])[CH:10]=1)([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 1012932-Bromo-5-nitroanisole

Product 1

HCID 147748372-Methoxy-4-nitro-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

50 ml of a 2M aqueous solution of sodium carbonate is added to a solution containing 12 g of 2-bromo 5-nitro anisole, 8.2 g of phenylboronic acid and 1.2 g of tetra(triphenylphosphine) palladium. The whole is heated under reflux for 7 hours, under vigorous agitation. The reaction medium is left to return to 20° C., it is poured into water and extraction is carried out with ethyl acetate. The organic phases are collected, dried and evaporated under reduced pressure. The product obtained is chromatographed on silica, eluting with a heptane-isopropyl ether mixture (9-1) and in this way 11.4 g of sought product is obtained, melting at 71° C.

Workup

  1. temperatureThe whole is heated
  2. temperatureunder reflux for 7 hours, under vigorous agitation
  3. waitThe reaction medium is left
  4. customto return to 20° C.
  5. customThe organic phases are collected
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe product obtained
  9. customis chromatographed on silica
  10. washeluting with a heptane-isopropyl ether mixture (9-1) and in this way 11.4 g of sought product
  11. customis obtained

Sources & evidence

ORD record
ord-d8621e3bc58a4fdd98ebcfeedcc96437
Source dataset
uspto-grants-1999_11
Patent number
US05985853

Reaction notes

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