Iodine → HCID 178447835, compound

HRID 2309304Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([F:14])[CH:3]=1.[Mg].II.[CH2:18]([C@H:21]1[CH2:26][CH2:25][C@H:24](CC(Cl)=O)[CH2:23][CH2:22]1)[CH2:19][CH3:20]>O1CCCC1.O>[F:14][C:4]1[CH:3]=[C:2]([C@H:24]2[CH2:25][CH2:26][C@H:21]([CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of 4-bromo-2-fluorobiphenyl (38.1 gram) in tetrahydrofuran (60 ml) was added over 20 minutes to magnesium turnings (4 gram) suspended in tetrahydrofuran (20 ml), reaction being initiated by adding a crystal of iodine and warming as usual. This Grignard reagent was now added to a solution of trans-4-propylcyclohexylacetyl chloride (40 gram) and cuprous chloride (0.4 gram) in tetrahydrofuran (200 ml) with stirring at -60° C. over 90 minutes. After allowing to warm to room temperature over two hours, the mixture was decomposed with water and the product extracted with petroleum ether (bpt. 60°-80°). The crude material was recrystallized twice from ethanol at 5° C. to give the product (20.6 gram, 40% theory), m.p. 96.5°-97.3° C., which was found to be 99.6 pure by glc.

Workup

customreaction being
temperaturewarming as usual
temperatureto warm to room temperature over two hours
extractionthe product extracted with petroleum ether (bpt. 60°-80°)
customThe crude material was recrystallized twice from ethanol at 5° C.
customto give the product (20.6 gram, 40% theory), m.p. 96.5°-97.3° C., which

Sources & evidence

ORD record: ord-cff131191944477eaa53b0f9fa9fe91f
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04695131

Reaction notes

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