Phenol → HCID 89581246, compound

HRID 1501072Notes

Reaction equation

HRID 1501072 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH:10]([CH3:11])[CH3:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 60798668HCID 60798668, compound

Product 1

HCID 89581246HCID 89581246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(4-bromophenyl)-3-methylbutan-1-ol (500 mg, 2.06 mmol), phenol (252 mg, 2.69 mmol) and triphenyl phosphine (1.06 g, 4.04 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred at room temperature under nitrogen atmosphere. After 1 hour, the mixture was cooled to 0° C. Diisopropyl azodicarboxylate (500 mg, 2.48 mmol) was added dropwise and the reaction was stirred at room temperature for 18 hours. The mixture was concentrated to give a residue and the residue was purified by column chromatography (silica gel, pure ether) to 1-bromo-4-(3-methyl-1-phenoxybutyl)benzene (300 mg, 46%).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customthe residue was purified by column chromatography (silica gel, pure ether) to 1-bromo-4-(3-methyl-1-phenoxybutyl)benzene (300 mg, 46%)

Sources & evidence

ORD record
ord-fc78fc8a6d7f46c49874e8ffeae62aa8
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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