p-Bromochlorobenzene → (4-Chlorophenyl)(4-cyanophenyl)methanol

HRID 561498Notes

Reaction equation

HRID 561498 reaction equation
[Mg].BrC(Br)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1.[C:14]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1)#[N:15]>O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:20]([OH:21])[C:19]2[CH:22]=[CH:23][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 112011,1-DibromoethaneHCID 660424-CyanobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 67001080(4-Chlorophenyl)(4-cyanophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.67 g (27.42 mmol) of magnesium turnings were dried by heating under argon and, after cooling to RT, 30 ml of tetrahydrofuran and 2 ml of dibromoethane were added. At 0° C., 5.00 g (26.12 mmol) of 4-chlorobromobenzene in 30 ml of tetrahydrofuran were slowly added to the mixture, and the mixture was stirred at RT for 30 min. Addition of 3.77 g (28.73 mmol) of 4-cyanobenzaldehyde in 30 ml of tetrahydrofuran was followed by stirring for 3 h. The THF was removed from the reaction solution in a rotary evaporator, and the residue was taken up in dichloromethane. It was washed with 1N hydrochloric acid, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The precipitate which separated out of the oily residue was filtered off, washed with diethyl ether and then purified by preparative HPLC (mobile phase: acetonitrile/water gradient). Acetonitrile was removed from the product-containing fractions in a rotary evaporator, and the aqueous residue was extracted with dichloromethane. Removal of the solvent resulted in 1.43 g (23% of theory) of the title compound.

Workup

  1. temperatureby heating under argon
  2. stirringby stirring for 3 h
  3. customThe THF was removed from the reaction solution in a rotary evaporator
  4. washIt was washed with 1N hydrochloric acid
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo
  8. customThe precipitate which separated out of the oily residue
  9. filtrationwas filtered off
  10. washwashed with diethyl ether
  11. custompurified by preparative HPLC (mobile phase: acetonitrile/water gradient)
  12. customAcetonitrile was removed from the product-containing fractions in a rotary evaporator
  13. extractionthe aqueous residue was extracted with dichloromethane
  14. customRemoval of the solvent

Sources & evidence

ORD record
ord-0bcd45a8d4d3459e937132ea90116bf3
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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