Phenol → HCID 89582638, compound

HRID 1501083Notes

Reaction equation

HRID 1501083 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6][CH2:5]2.[C:13]1(O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 184699326-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 89582638HCID 89582638, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (0.68 g, 3.0 mmol) and phenol (0.38 g, 4.0 mmol) in anhydrous tetrahydrofuran (10 mL) was added triphenylphosphine (1.04 g, 4 mmol). The reaction mixture was stirred at room temperature for 0.5 hour under nitrogen atmosphere. Then diisopropyl azodicarboxylate (0.8 g, 4 mmol) was added dropwise at 0° C., and then the reaction mixture was stirred at room temperature for 12 hours. After the reaction, it was quenched with water (100 mL), and the product was extracted with ethyl acetate (100 mL), dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product 6-bromo-1-phenoxy-1,2,3,4-tetrahydro naphthalene (0.73 g, 80%). 1H NMR (300 MHz, CDCl3): δ 7.32-7.20 (m, 5H), 7.00-6.97 (m, 3H), 5.27 (t, J=4.5 Hz, 1H), 2.86-2.67 (m, 2H), 2.11-1.74 (m, 4H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction, it
  3. customwas quenched with water (100 mL)
  4. extractionthe product was extracted with ethyl acetate (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20)

Sources & evidence

ORD record
ord-9078a5dd6c1742e5b3ef95fd23ec1ecd
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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