1-Bromo-4-iodobenzene → HCID 178501088, compound

HRID 530374Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[C:9]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1)(=[O:11])[CH3:10].[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]2)([OH:11])[CH3:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Isopropylmagnesium chloride-lithium chloride complex (8.35 mL, 10.9 mmol) was added to a cooled solution of 1-bromo-4-iodobenzene (3.07 g, 10.9 mmol) in THF (8 mL) and the resultant solution was stirred for 1 hour at 0° C. Methyl trans-4-acetylcyclohexanecarboxylate (1.00 g, 5.43 mmol) in THF (2 mL) was added to the reaction mixture, stirred for 1 hour at 0° C. and saturated aqueous ammonium chloride was added. The reaction mixture was extracted with ethyl acetate (2×), and then the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography (ethyl acetate/hexanes) gave methyl trans-4-[1-(4-bromophenyl)-1-hydroxyethyl]cyclohexanecarboxylate as a colorless oil. MS ESI calcd. for C16H22BrO3[M+H]+341 and 343. found 341 and 343. 1H NMR (500 MHz, CDCl3) δ 7.44 (d, J=8.5 Hz, 2H), 7.26 (d, J=8.4 Hz, 2H), 3.63 (s, 3H), 2.16 (tt, J=12.3 Hz, 3.6 Hz, 1H), 2.03-1.91 (m, 2H), 1.84 (m, 1H), 1.60-1.53 (m, 2H), 1.52 (s, 3H), 1.36 (m, 2H), 1.11-0.98 (m, 2H).

Workup

extractionThe reaction mixture was extracted with ethyl acetate (2×)
dry with materialthe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified via silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-96c4d8df6f2d4ce8a93659b8db613aa8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353066B2

Reaction notes

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