Sodium Carbonate → 5-[4-(5-Formylfuran-2-yl)-phenyl]-furan-2-carboxaldehyde

HRID 422119

Reaction equation

Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]([O-:12])([O-])=O.[Na+].[Na+].[C:15]1(B(O)O)[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>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:7]([C:5]1[O:6][C:2]([C:15]2[CH:20]=[CH:19][C:18]([C:5]3[O:6][C:2]([CH:9]=[O:12])=[CH:3][CH:4]=3)=[CH:17][CH:16]=2)=[CH:3][CH:4]=1)=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 5-bromofuran-2-carboxaldehyde (10 mmol), and tetrakis(triphenylphosphine) palladium (400 mg) in toluene (20 mL) under a nitrogen atmosphere was added 10 mL of a 2 M aqueous solution of Na2CO3 followed by 1,4-phenylenebisboronic acid (5 mmol) in 6 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 (300 mL) and 2 M aqueous Na2CO3 (15 mL) containing 5 mL of concentrated ammonia. The organic layer was dried (Na2SO4), and then concentrated to dryness under reduced pressure to afford 11 in 93% yield; mp 233-234° C. (EtOH). 1H NMR (DMSO-d6); δ 9.64 (s, 2H), 8.01 (s, 4H), 7.70 (d, J=3.6 Hz, 2H), 7.43 (d, J=3.6 Hz, 2H). MS (ESI) m/e (rel. int.): 266 (M+, 100), 238 (5), 209 (25). Anal. Calc. for C16H10O4: C %, 72.16; H %, 3.78. Found C %, 72.41; H %, 3.93.

Workup

customThe solvent was evaporated
customthe precipitate was partitioned between methylene chloride (300 mL) and 2 M aqueous Na2CO3 (15 mL)
additioncontaining 5 mL of concentrated ammonia
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-34fc8fd2915d4769b123fdcd721bc010
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101636B2

Linked notes

Loading…