4-Bromo-2-chloro-1-iodobenzene → HCID 67313561, compound

HRID 1012665Notes

Reaction equation

HRID 1012665 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([Cl:9])[CH:3]=1.C([Mg]Cl)(C)C.[Cl:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:17]=1[CH:18]=[O:19]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:18]([C:17]2[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:16]=2[Cl:15])[OH:19])=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 27355474-Bromo-2-chloro-1-iodobenzeneHCID 129278382-Chloro-5-methoxybenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 67313561HCID 67313561, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a solution of 4-bromo-2-chloro-1-iodo-benzene (10.0 g, 31.5 mmol) in THF (120 ml) was added 2 M solution of isopropylmagnesium chloride in THF (17.3 ml, 34.60 mmol) at −65° C. The reaction mixture was stirred at −40° C. for 20 min. After 2-chloro-5-methoxy-benzaldehyde (5.5 g, 32.20 mmol) was added, the reaction mixture was warmed to room temperature and stirred overnight. Then the solution was quenched with saturated aqueous solution of NH4Cl. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude material was purified by chromatography (petroleum ether/CH2Cl2 1:1) to provide title compound as a yellowish oil.

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. stirringstirred overnight
  3. customThen the solution was quenched with saturated aqueous solution of NH4Cl
  4. extractionThe aqueous phase was extracted twice with diethyl ether
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by chromatography (petroleum ether/CH2Cl2 1:1)

Sources & evidence

ORD record
ord-cf95ca44ea03494d8189001044ecf14b
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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