Sodium Carbonate → HCID 18357511, compound

HRID 428041Notes

Reaction equation

HRID 428041 reaction equation
O1C=CC=C1B(O)O.Br[C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].C(=O)([O-])[O-].[Na+].[Na+].[C:24]1(C)[C:25]([CH2:30][CH2:31][OH:32])=[CH:26][CH:27]=[CH:28][CH:29]=1>C(Cl)Cl.[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>[O:32]1[C:31]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=[O:13])=[CH:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]1=2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 811292-BromobenzaldehydeHCID 882672-Methylphenethyl alcoholHCID 2734357Furan-2-boronic acid

Product 1

HCID 18357511HCID 18357511, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3 g of benzolb]furan-2-boronic acid, 3.14 g 2-bromobenzaldehyde, 0.56 g tetrakis(triphenylphosphine)-palladium (0), and 17 ml of 2N aqueous sodium carbonate in 50 ml of a 9:1 mixture of toluene-ethanol, under a nitrogen atmosphere, was heated to 100° C. for 10 h. The mixture was cooled to room temperature, diluted with 100 ml of methylene chloride and washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 2-(benzo[b]furan-2-yl)benzaldehyde as a brown gum, GC-M.S. (E.I.) (M/Z): 222 [M+].

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-86fb0f718ada46b2bc17acf4d0193229
Source dataset
uspto-grants-2001_11
Patent number
US06313139B1

Reaction notes

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