Toluene → HCID 23031649, compound

HRID 422956Notes

Reaction equation

HRID 422956 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]1([CH2:15]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][C:5]([O:8][CH2:15][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14946075HCID 14946075, compound

Product 1

HCID 23031649HCID 23031649, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromophenol (6.0 g, 34.7 mmol), cyclohexylmethylphenol (4.3 ml, 34.7 mmol) and triphenylphosphine (9.1 g, 34.7 mmol) in tetrahydrofuran (100 ml) was added slowly a 40% solution of diethyl azodicarboxylate in toluene (15.1 ml, 34.7 mmol) in portions at 0° C. with stirring, and then the resulting mixture was stirred at room temperature for 3 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 (1:20) as the eluent to afford 1-bromo-4-(cyclohexylmethoxy)benzene (5.1 g, yield: 54%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 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-606a11e7031d41abb5889afe0e0a3322
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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