Sodium Carbonate → HCID 18357511, compound

HRID 1422146Notes

Reaction equation

HRID 1422146 reaction equation
[O:1]1[C:5](B(O)O)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.Br[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C(CCO)=CC=CC=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:1]1[C:5]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[CH:16]=[O:17])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 811292-BromobenzaldehydeHCID 882672-Methylphenethyl alcoholHCID 2776266Benzo[b]furan-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 benzo[b]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-0d7c42c70e58473a99e2a6949006a48b
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

Loading…