1,3-Dibromobenzene → HCID 22328599, compound

HRID 586125Notes

Reaction equation

HRID 586125 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[Li]CCCC.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1>C1COCC1.CCCCCC>[Br:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:20]([OH:21])[C:19]1[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 79271,3-DibromobenzeneHCID 312444-MethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 22328599HCID 22328599, compoundYield 1,756.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred −78° solution of m-dibromobenzene (70.9 g, 0.3 mol) in 200 mL of dry THF under Ar was added 117 mL of 2.56 M n-BuLi (0.3 mol) in hexane over 10 min. After 30 min, p-methoxybenzaldehyde (27.2 g, 0.02 mol) in 50 mL of THF was added over 20 min. The solution was stirred for 1 hr at −78° (complete by tlc) prior to quenching with saturated aq. NH4Cl. After warming to 20°, the reaction was diluted 2 fold with EtOAc prior to washing with H2O followed by brine. After drying over Na2SO4 and concentration using a rotary evaporator, 103 g of 3-bromo-4′-methoxybenzhydrol was obtained as a yellow oil that was carried forward without further purification.

Workup

  1. customto quenching with saturated aq. NH4Cl
  2. temperatureAfter warming to 20°
  3. additionthe reaction was diluted 2 fold with EtOAc
  4. washto washing with H2O
  5. dry with materialAfter drying over Na2SO4 and concentration
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-618c82ca1dd64b9d916744f1708a3705
Source dataset
uspto-grants-2005_08
Patent number
US06936590B2

Reaction notes

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