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

HRID 1513112Notes

Reaction equation

HRID 1513112 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([CH2:15]O)[CH2:14][CH2:13][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][CH2:15][CH:10]2[CH2:14][CH2:13][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 77195Cyclopentanemethanol

Product 1

HCID 671714831,3-Dibromo-5-(cyclopentylmethoxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,5-Dibromophenol (5.0 g; 19.8 mmol), cyclopentane-methanol (2.0 g; 19.9 mmol) and tributylphosphine (8.8 mL; 35.7 mmol) were dissolved in dry THF (250 mL) in a dried reaction flask under an atmosphere of nitrogen. 1,1′-(Azodicarbonyl)dipiperidine (9.01 g; 35.7 mmol) dissolved in dry THF (150 mL) was added to the reaction mixture, which was stirred at room temperature for 16 hours. The reaction mixture was filtered, evaporated to dryness and purified by flash chromatography (heptane→ethyl acetate:heptane 2:3). Yield: 5.68 g; 86%.

Workup

  1. additionwas added to the reaction mixture, which
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. custompurified by flash chromatography (heptane→ethyl acetate:heptane 2:3)

Sources & evidence

ORD record
ord-f01b755c80284fc28867413f8208ba48
Source dataset
uspto-grants-2012_07
Patent number
US08217086B2

Reaction notes

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