1,4-Dibromo-2,5-bis(hexyloxy)benzene → HCID 19362111, compound

HRID 376480Notes

Reaction equation

HRID 376480 reaction equation
[Li]CCCC.[CH2:6]([O:12][C:13]1[CH:18]=[C:17]([Br:19])[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][C:14]=1Br)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C1COCC1>[CH2:21]([O:20][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:18][C:17]=1[Br:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 167262041,4-Dibromo-2,5-bis(hexyloxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 19362111HCID 19362111, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under N2 and at -78° C., n-BuLi (23.8 mL, 2.5M in hexanes) was added, over 30 min, to a solution of 1,4-dihexyloxy-2,5-dibromobenzene (25.92 g., 59.45 mmol) in THF (150 mL). After the addition, the reaction mixture was stirred at -78° C. for 1 h and was then quenched with aq. NH4Cl at -78° C. After the usual workup, 1,4-dihexyloxy-2-bromobenzene was obtained as a pale yellow liquid (97% yield).

Workup

  1. additionAfter the addition
  2. customwas then quenched with aq. NH4Cl at -78° C

Sources & evidence

ORD record
ord-598655cb1815440ca05d83065e52f9d6
Source dataset
uspto-grants-2000_02
Patent number
US06020452

Reaction notes

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