Potassium Carbonate → 6-Nitrobiphenyl-2-carbaldehyde

HRID 659654Notes

Reaction equation

HRID 659654 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.CCOCC.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+:10]([C:9]1[CH:8]=[CH:7][CH:6]=[C:3]([CH:4]=[O:5])[C:2]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 126677132-Chloro-3-nitrobenzaldehyde

Product 1

HCID 541378936-Nitrobiphenyl-2-carbaldehydeYield 82.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A 250-mL 3-necked round-bottom flask was placed a solution of 2-chloro-3-nitrobenzaldehyde (5.3 g, 28.57 mmol, 1.00 equiv) in toluene (50 mL), phenylboronic acid (3.83 g, 31.39 mmol, 1.10 equiv), K2CO3 (7.88 g, 57.10 mmol, 2.00 equiv) in water (30 mL) and Pd(PPh3)4 (660 mg, 0.57 mmol, 0.02 equiv). The resulting mixture was heated to 110° C. for 30 hours. Upon completion, the reaction mixture was cooled and diluted with Et2O (1000 mL). After phase separation, organic layers were dried over anhydrous magnesium sulfate, filtered off and concentrated on rotary evaporator. The residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:50) affording 6-nitrobiphenyl-2-carbaldehyde as yellow solid (5.35 g, 82%).

Workup

  1. customA 250-mL 3-necked round-bottom flask was placed
  2. temperatureUpon completion, the reaction mixture was cooled
  3. customAfter phase separation, organic layers
  4. dry with materialwere dried over anhydrous magnesium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated on rotary evaporator
  7. customThe residue was purified by a silica gel column chromatography
  8. washeluted with ethyl acetate/petroleum ether (1:50)

Sources & evidence

ORD record
ord-4e80ae11deee4b59aba4997054349fee
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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