Bromine → 2-Methylbutyloxy-3-bromo-4-hydroxybiphenyl

HRID 648875Notes

Reaction equation

HRID 648875 reaction equation
[CH3:1][CH:2]([CH2:18][CH3:19])[CH2:3][O:4]C1C=CC(C2C=CC(O)=CC=2)=CC=1.CC(CC)CO[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([Br:37])[CH:31]=2)=[CH:26][CH:25]=1.BrBr>O1CCOCC1>[CH3:1][CH:2]([CH2:18][CH3:19])[CH2:3][O:4][C:31]1[C:32]([Br:37])=[C:33]([OH:36])[CH:34]=[CH:35][C:30]=1[C:27]1[CH:26]=[CH:25][CH:24]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 140938154'-(2-Methylbutoxy)(1,1'-biphenyl)-4-olHCID 201439964'-(2-Methylbutyloxy)-3-bromo-4-hydroxybiphenyl

Product 1

HCID 1317154892-Methylbutyloxy-3-bromo-4-hydroxybiphenyl

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
40 °C

Procedure

4'-(2-Methylbutyloxy)-4-hydroxybiphenyl (15 g) obtained in Example 1, (i) was dissolved in 1,4-dioxane (50 ml), followed by dropwise adding a mixture of bromine (10.5 g) and 1,4-dioxane (140 ml), heating on a water bath at 40° C. for 4 hours with stirring, thereafter distilling off 1,4-dioxane under reduced pressure, adding toluene (300 ml) to the remaining solution, adding a 10% aqueous solution of sodium hydrogen sulfite till the color of bromine disappeared, three times washing with saturated aqueous solution of NaCl to make the liquid neutral, drying and distilling off toluene to obtain a raw product of 4'-(2-methylbutyloxy-3-bromo-4-hydroxybiphenyl (21 g).

Workup

  1. additionby dropwise adding
  2. distillationdistilling off 1,4-dioxane under reduced pressure
  3. additionadding toluene (300 ml) to the remaining solution
  4. additionadding a 10% aqueous solution of sodium hydrogen sulfite till the color of bromine
  5. washthree times washing with saturated aqueous solution of NaCl
  6. customdrying
  7. distillationdistilling off toluene

Sources & evidence

ORD record
ord-57b4796159e94c02a4489197e9942eae
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Reaction notes

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