Bromobenzene → HCID 7302306, compound

HRID 523348Notes

Reaction equation

HRID 523348 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[C:9]([O:24][C@@H:25]1[CH2:30][C@H:29]([CH3:31])[CH2:28][CH2:27][C@H:26]1[CH:32]([CH3:34])[CH3:33])(=[O:23])[C:10]([O:12][C@@H]1C[C@H](C)CC[C@H]1C(C)C)=O>C1COCC1>[O:12]=[C:10]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([O:24][C@@H:25]1[CH2:30][C@H:29]([CH3:31])[CH2:28][CH2:27][C@H:26]1[CH:32]([CH3:33])[CH3:34])=[O:23]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 5462224MagnesiumHCID 11383005Ethanedioic acid, 1,2-bis[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester, rel-

Product 1

HCID 7302306HCID 7302306, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent prepared from bromobenzene (2.36 g, 15.0 mmol) and magnesium (0.39 g, 16.0 mmol) in THF (25 ml) was added dropwise to a stirred solution of bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) oxalate (5.00 g, 13.7 mmol) in THF (25 ml) at −78° C. The mixture was slowly warmed to room temperature, quenched with a saturated solution of NH4Cl (50 ml) and ice. The reaction mixture was extracted with ether (2×) and water (2×) and the organic phase dried (Na2SO4). Repetitive column chromatography (SiO2, heptane/ether 9:1) gave 1.28 g (32%) of the pure product as a slightly yellow oil.

Workup

  1. customquenched with a saturated solution of NH4Cl (50 ml) and ice
  2. extractionThe reaction mixture was extracted with ether (2×) and water (2×)
  3. dry with materialthe organic phase dried (Na2SO4)

Sources & evidence

ORD record
ord-05f9fc02d2254562afead8a2da14fbfd
Source dataset
uspto-grants-2016_05
Patent number
US09334464B2

Reaction notes

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