4-Chlorophenol → HCID 58307103, compound

HRID 1909875Notes

Reaction equation

HRID 1909875 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([OH:11])[CH:8]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([O:11][C:35]1[CH:36]=[CH:37][C:32]([Cl:31])=[CH:33][CH:34]=1)[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66868106HCID 66868106, compound

Product 1

HCID 58307103HCID 58307103, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 7-bromoinden-1-ol (1.06 g), triphenylphosphine (1.86 g), 4-chlorophenol (911 mg), and toluene (30 mL) was added dropwise diethyl azodicarboxylate (2.2 M toluene solution, 3.3 mL) at room temperature. After dropwise addition, the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and then the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 7-bromo-1-(4-chlorophenoxy)indane (306 mg).

Workup

  1. additionAfter dropwise addition
  2. customThe solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1042263344824e4cb349c8884b52aa7b
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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