3-Bromofuran → HCID 19047515, compound

HRID 865944Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.CN(OC)[C:14]([C:16]1[CH:20]=[CH:19][O:18][CH:17]=1)=[O:15]>CCOCC>[O:9]1[CH:10]=[CH:11][C:7]([C:14]([C:16]2[CH:20]=[CH:19][O:18][CH:17]=2)=[O:15])=[CH:8]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of n-butyllithium (2.5M, 28 ml, 0.07 mol) in 150 ml of ether at -78° C. was added a solution of 3-bromofuran (10 g, 0.0628 mol) in 30 ml of ether over a 20 min period and the mixture was stirred at -78° C. for 20 min. To the above mixture was added 3-(N-methyl-N-methoxycarbamoyl)furan (9.16 g, 0.059 mol) in 30 ml of ether over a 15 min period and the mixture was stirred at room temperature for 1/2 h. The reaction mixture was quenched with 200 ml of ammonium chloride solution, 500 ml of methylene chloride was added and the mixture was stirred. The organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was triturated in 100 ml of hexane/t-butylmethylether (9:1). The solid product was filtered and washed with t-butylmethylether to afford 7.5 g (78.3%) of di-(3-furyl)ketone.

Workup

stirringthe mixture was stirred at room temperature for 1/2 h
customThe reaction mixture was quenched with 200 ml of ammonium chloride solution, 500 ml of methylene chloride
additionwas added
stirringthe mixture was stirred
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customthe residue was triturated in 100 ml of hexane/t-butylmethylether (9:1)
filtrationThe solid product was filtered
washwashed with t-butylmethylether

Sources & evidence

ORD record: ord-f6fc3e604a2443a7b8c955ec3f4aaf5d
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05569655

Reaction notes

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