1,4-Dibromobenzene → HCID 22349585, compound

HRID 896079Notes

Reaction equation

HRID 896079 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[Li]CCCC.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[C:19]([CH:22]=1)[CH:20]=[O:21]>C1COCC1>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[C:19]([CH:20]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[OH:21])[CH:22]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 906845-Bromo-2-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 22349585HCID 22349585, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1,4-Dibromobenzene (15.3 g; 65 mmol) in THF (350 ml) is cooled to −78° C. and treated with nBuLi (44.7 ml; 71.5 mmol of a 1.6M solution). The white precipitate is stirred for 15 minutes at −78° C. 5-Bromo-2-methoxy-benzaldehyde (6.98 g; 32.5 mmol) in THF (32 ml) is added, stirred for 5 min at −78° C. and then poured on water. The aqueous phase is extracted twice with TBME, the organic phase dried over Na2SO4, evaporated to dryness and the residue purified via SiO2 chromatography (Cyclohexane/acetone 98:2>96:4) to yield the title compound as white crystals recrystallised from ether/hexanes (9.25 g; 73.8%).

Workup

  1. stirringstirred for 5 min at −78° C.
  2. additionpoured on water
  3. extractionThe aqueous phase is extracted twice with TBME
  4. dry with materialthe organic phase dried over Na2SO4
  5. customevaporated to dryness
  6. customthe residue purified via SiO2 chromatography (Cyclohexane/acetone 98:2>96:4)

Sources & evidence

ORD record
ord-66981086a8ae413582db01627be07d4b
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Reaction notes

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