Sodium Carbonate → 5-(4′-Formyl[1,1′-biphenyl]-4-yl)-2-furancarboxaldehyde

HRID 422116Notes

Reaction equation

HRID 422116 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22]>C1(C)C=CC=CC=1.CO.[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>[CH:21]([C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:25][CH:24]=1)=[O:22]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 6195775-(4-Bromophenyl)furfural

Product 1

HCID 118498505-(4′-Formyl[1,1′-biphenyl]-4-yl)-2-furancarboxaldehydeYield 85%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-(4-bromophenyl)-furan-2-carboxaldehyde (5 mmol), and tetrakis(triphenylphosphine) palladium (200 mg) in toluene (10 mL) under a nitrogen atmosphere was added 5 mL of a 2 M aqueous solution of Na2CO3 followed by 4-formylphenylboronic acid (6 mmol) in 5 mL of methanol. The vigorously stirred mixture was warmed to 80 ° C. for 12 h. The solvent was evaporated, the precipitate was partitioned between methylene chloride (200 mL) and 2 M aqueous Na2CO3 (15 mL) containing 3 mL of concentrated ammonia. The organic layer was dried (Na2SO4), and then concentrated to dryness under reduced pressure to afford 1 in 85% yield; mp 173-174 ° C. (SiO2, hexanes/EtOAc, 70:30). 1H NMR (DMSO-d6); δ 7.42 (d, J=3.6 Hz, 1H), 7.70 (d, J=3.6 Hz, 1H), 7.93-8.01 (m, 8H), 9.64 (s, 1H), 10.07 (s, 1H). 13C NMR (DMSO-d6); δ 192.7, 177.9, 157.6, 151.8, 144.6, 139.6, 135.3, 130.2, 128.6, 127.9, 127.3, 125.7, 109.5. MS (ESI) m/e (rel. int.): 276 (M+, 100), 247 (5), 219 (25), 189 (25). Anal. Calc. for C8H12O3: C %, 78.24; H %, 4.37. Found C %, 77.99; H %, 4.44.

Workup

  1. customThe solvent was evaporated
  2. customthe precipitate was partitioned between methylene chloride (200 mL) and 2 M aqueous Na2CO3 (15 mL)
  3. additioncontaining 3 mL of concentrated ammonia
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated to dryness under reduced pressure
  6. customto afford 1 in 85% yield

Sources & evidence

ORD record
ord-5eb1ac702f3145e7bdb923ad0e067281
Source dataset
uspto-grants-2012_01
Patent number
US08101636B2

Reaction notes

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