4-Chlorophenol → 1-(2-Bromoethoxy)-4-chlorobenzene

HRID 1374849Notes

Reaction equation

HRID 1374849 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Br:9][CH2:10][CH2:11][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 748541-(2-Bromoethoxy)-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorophenol (500 mg, 3.89 mg), 2-bromoethanol (0.28 ml, 3.89 mmol), triphenylphosphine (1.02 g, 3.89 mmol) were dissolved in tetrahydrofuran (8 ml). The solution was added dropwise with diisopropylazodicarboxylate (0.84 ml, 3.89 mmol) and stirred at room temperature for 3 hours. The solvent of the reaction mixture was evaporated, and then solids were precipitated by using diethyl ether-hexane and removed by filtration. The filtrate was evaporated under reduced pressure to obtain the title compound as crude product (1.18 g). The crude product was used for the next reaction without purification.

Workup

  1. customThe solvent of the reaction mixture was evaporated
  2. customsolids were precipitated
  3. customremoved by filtration
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9619f50217e9463698264b8ff6bce10a
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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