Tetrahydrofuran → HCID 19063902, compound

HRID 482282Notes

Reaction equation

[Cl:1][C:2]1C=C(Cl)C=C[C:3]=1[C:4]([Cl:6])=O.[CH2:12]([Mg]Br)[CH2:13][CH3:14].[O:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>[Cu]I>[Cl:1][CH:2]([CH2:3][CH2:4][Cl:6])[C:21]([C:20]1[CH:14]=[CH:13][CH:12]=[CH:18][CH:19]=1)=[O:17]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2,4-dichlorobenzoyl chloride (4.5 g, 21.5 mmol) in tetrahydrofuran (30 ml) was treated with copper (I) iodide (200 mg) and cooled to -20° C. Propyl magnesium bromide (2.0M in diethyl ether, 11 ml, 11 mmol) was slowly injected (10 minutes) under nitrogen. The yellow suspension was stirred at -20° C. to -15° C. for 10 minutes, the cooling bath was removed and stirring was continued for another hour. The reaction was quenched with water, and the product was extracted with toluene. The organic phase was washed with 1N aqueous hydrochloric acid, bicarbonate and brine, filtrated through a silica gel pad and concentrated in vacuo to give 2,4-dichlorobutyrophenone as a yellowish oil (4.5 g, 96%) which was used in the next step without further purification. 1H NMR (CDCl3): 0.99 (t, 3H), 1.74 (m, 2H), 2.91 (t, 2H), 7.32 (d, 1H), 7.42 (d, 1H), 7.44 (s, 1H).

Workup

custom(10 minutes)
customthe cooling bath was removed
stirringstirring
waitwas continued for another hour
customThe reaction was quenched with water
extractionthe product was extracted with toluene
washThe organic phase was washed with 1N aqueous hydrochloric acid, bicarbonate and brine
filtrationfiltrated through a silica gel pad
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-11a75c6d7674442cb4d65ba9c705ba1d
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05795905

Reaction notes

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