1-Bromo-4-iodobenzene → Bromadol

HRID 351332Notes

Reaction equation

HRID 351332 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH:9]([Mg]Cl)([CH3:11])[CH3:10].[CH3:14][N:15]([CH3:28])[C:16]1(C#N)[CH2:25][CH2:24][C:19]2([O:23]CCO2)[CH2:18][CH2:17]1.[Cl-].[NH4+]>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]2([N:15]([CH3:14])[CH3:28])[CH2:17][CH2:18][C:19]([CH2:10][CH2:9][C:11]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)([OH:23])[CH2:24][CH2:25]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 115221-Bromo-4-iodobenzeneHCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 9887338Bromadol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

26.6 g 4-bromoiodobenzene were placed in 150 ml diethylether and 47 ml 2.0 molar isopropyl magnesium chloride solution were added dropwise at ambient temperature. After one further hour, 18 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile, dissolved in 250 ml diethylether, were added dropwise and stirred overnight. To work up the mixture with ice cooling, 20 ml ammonium chloride solution (20% by weight) were added, extracted three times with 100 ml diethylether in each case, the combined organic phases were dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. The crude product (21.8 g) obtained was chromatographed with diethylether over silica gel. 7.49 g 4-(4-bromophenyl)-4-dimethylamino-1-phenethylcyclohexanol were obtained as a colorless liquid.

Workup

  1. additionwere added dropwise
  2. additionwere added
  3. extractionextracted three times with 100 ml diethylether in each case
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product (21.8 g) obtained
  8. customwas chromatographed with diethylether over silica gel

Sources & evidence

ORD record
ord-81f784e77b854c798da774a2739ec1c0
Source dataset
uspto-grants-2007_02
Patent number
US07183436B2

Reaction notes

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