Boron tribromide → 4-[5-(Octyloxy)pyridin-2(1H)-ylidene]cyclohexa-2,5-dien-1-one

HRID 1768884Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 11C (100 mg) in dichloromethane, cooled to 0° C., was added a solution of boron tribromide in dichloromethane (1M, 0.76 ml). This solution was stirred at 0° C. for 4 hours, then allowed to stand at 4° C. an additional 16 hrs. The solution was then poured into a saturated sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and the solvent removed in vacuo to give a white solid.

Workup

waitto stand at 4° C. an additional 16 hrs
extractionextracted with dichloromethane
dry with materialThe combined organic layers were dried over sodium sulfate
customthe solvent removed in vacuo
customto give a white solid

Sources & evidence

ORD record: ord-6fe9523c45544fe2b992c7cff95cafed
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380460

Reaction notes

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