Phenol → 1-Bromo-2-chloro-4-(1-phenoxyethyl)benzene

HRID 1501129Notes

Reaction equation

HRID 1501129 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[Cl:11].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:9])=[CH:4][C:3]=1[Cl:11]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 895810881-(4-Bromo-3-chlorophenyl)ethanol

Product 1

HCID 1185627221-Bromo-2-chloro-4-(1-phenoxyethyl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-bromo-3-chlorophenyl)ethanol (1.32 g, 5.6 mmol), phenol (525 mg, 5.6 mmol) and triphenylphosphine (2198 mg, 8.4 mmol) in tetrahydrofuran (30 mL) was stirred at room temperature for 0.5 hour. Diisopropyl azodicarboxylate (1695 mg, 8.4 mmol) was dropwise to the reaction mixture and was stirred at room temperature for 12 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=5:1) to give 1-bromo-2-chloro-4-(1-phenoxyethyl)benzene as a colorless oil (882 mg 54%). 1H NMR (300 MHz, CDCl3): 7.37 (d, J=8.1, 1H), 7.27-7.20 (m, 4H), 6.92-6.82 (m, 3H), 5.30 (q, J=6.6, 1H), 1.62 (d, J=6.6, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ba9d8bef50494770bf21503431425221
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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