Sodium Carbonate → 2-Nitrobiphenyl

HRID 718734Notes

Reaction equation

HRID 718734 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(COC)OC.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>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 113411-Bromo-2-nitrobenzeneHCID 66827Phenylboronic Acid

Product 1

HCID 68292-Nitrobiphenyl

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Aqueous sodium carbonate (2 M, 100 mL), followed by tetrakis(triphenylphosphine) palladium (340. mg, 0.297 mmol), were added to a solution of 2-bromonitrobenzene (2.00 g, 9.90 mmol) and phenylboronic acid (1.27 g, 9.90 mmol) in dimethoxyethane (125 mL). The reaction mixture was heated to reflux for 3 hours. The reaction crude was then cooled to room temperature, diluted with water (100 mL) and the product extracted with CH2Cl2 (4×50 mL). The organic phase was dried over MgSO4, and concentrated under reduced pressure to yield a yellow solid, which was further purified via flash chromatography over silica, eluting with a gradient of hexanes to 20% CHCl3/80% hexanes. The nitro 2 was obtained as a yellow oil that was further dried under high vacuum for 24 h (1.79 g, 90.1%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe reaction crude
  4. extractionthe product extracted with CH2Cl2 (4×50 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto yield a yellow solid, which
  8. customwas further purified via flash chromatography over silica
  9. washeluting with a gradient of hexanes to 20% CHCl3/80% hexanes

Sources & evidence

ORD record
ord-1f3427dc112f43acbf5cdf744e6741f6
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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