Toluene → HCID 23031435, compound

HRID 422957Notes

Reaction equation

HRID 422957 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH:9]1([CH2:15][CH2:16]C2C=CC=CC=2O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:16][CH2:15][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:3]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 115633-BromophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10845876HCID 10845876, compound

Product 1

HCID 23031435HCID 23031435, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromophenol (15.0 g, 86.7 mmol), 2-cyclohexylethylphenol (12.0 ml, 86.7 mmol) and triphenylphosphine (23.0 g, 86.7 mmol) in tetrahydrofuran (200 ml) was added slowly a 40% solution of diethyl azodicarboxylate in toluene (38.0 ml, 86.7 mmol) in portions at 0° C. with stirring, and then the resulting mixture was stirred at room temperature for 7 hours. After stirring, the reaction mixture was evaporated in vacuo, and hexane was added to the residue. After filtration, the filtrate was evaporated in vacuo once again, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:100) as the eluent to afford 1-bromo-3-(2-cyclohexylethoxy)benzene (23.0 g, yield: 94%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 7 hours
  2. stirringAfter stirring
  3. customthe reaction mixture was evaporated in vacuo, and hexane
  4. additionwas added to the residue
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated in vacuo once again
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0990dc18f04e4e359e712364683b3497
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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