3,5-Dibromophenol → 1,3-Dibromo-5-(cyclopropylmethoxy)benzene

HRID 1969203Notes

Reaction equation

HRID 1969203 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH:10]1([CH2:13]O)[CH2:12][CH2:11]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:13][CH:10]2[CH2:12][CH2:11]2)[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

6

Reactant 4

HCID 122803,5-DibromophenolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 75644Cyclopropanemethanol

Product 1

HCID 670243041,3-Dibromo-5-(cyclopropylmethoxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,5-Dibromo-phenol (5 g; 19.9 mmol), cyclopropylcarbinol (1.4 g; 19.9 mmol) and tributylphosphine (8.8 mL; 35.7 mmol) were dissolved in THF (500 mL) in a dried reaction flask under an atmosphere of nitrogen. 1,1′-(Azodicarbonyl)dipiperidine (9.0 g; 35.7 mmol) dissolved in THF (100 mL) was added to the reaction mixture, which was stirred at room temperature for 16 hours. The reaction mixture was partly evaporated, filtered, evaporated to dryness and purified by flash chromatography (ethyl acetate:heptane 0:1→1:10). Yield: 5.45 g; 90%.

Workup

  1. additionwas added to the reaction mixture, which
  2. customThe reaction mixture was partly evaporated
  3. filtrationfiltered
  4. customevaporated to dryness
  5. custompurified by flash chromatography (ethyl acetate:heptane 0:1→1:10)

Sources & evidence

ORD record
ord-b21f632a1cdc4f05b718bf73ba53e3b7
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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