Phenol → HCID 118562723, compound

HRID 1501133Notes

Reaction equation

HRID 1501133 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:9])=[C:4]([CH3:11])[CH:3]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68223692HCID 68223692, compound

Product 1

HCID 118562723HCID 118562723, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-(4-bromo-2-methylphenyl)ethanol (430 mg, 2 mmol), phenol (184 mg, 2 mmol), triphenylphosphine (655 mg, 2.5 mmol) in tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (505 mg, 2.5 mmol) at 0° C. The mixture was stirred at 20° C. for 12 hours. Water (15 mL) was added to the mixture and then extracted with ethyl acetate (35 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give 4-bromo-2-methyl-1-(1-phenoxyethyl)benzene (210 mg, 36%).

Workup

  1. extractionextracted with ethyl acetate (35 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-91eac7af453c4d46974bd762ff23f11a
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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