2-Bromophenol → 1-Bromo-2-[2-(4-fluorophenyl)ethoxy]benzene

HRID 2421342Notes

Reaction equation

HRID 2421342 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][CH2:34]O)=[CH:31][CH:30]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][CH2:34][O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 72442-BromophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 219143401-Bromo-2-[2-(4-fluorophenyl)ethoxy]benzeneYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromophenol (3.46 g) was mixed with tetrahydrofuran (60 ml) and triphenylphosphine (6.3 g) was added along with 4-fluorophenethyl alcohol (4.2 g). The mixture was cooled in an ice bath before dropwise addition of diisopropyl azodicarboxylate (4.85 g). The mixture was allowed to warm to room temperature over 18 h. The mixture was evaporated and diethyl ether (100 ml) was added. Stirring was continued for 3 h, the mixture was filtered and the filtrate was evaporated. The product was purified by column chromatography eluting with ethyl acetate/hexane mixtures to give a yellow oil (4.47 g).

Workup

  1. customThe mixture was evaporated
  2. additiondiethyl ether (100 ml) was added
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe product was purified by column chromatography
  6. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-ceed2bd0ca0b4d46822262198fcbc17f
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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