Phenol → HCID 69118208, compound

HRID 1501056Notes

Reaction equation

HRID 1501056 reaction equation
C(OC(N=NC(OC(C)C)=O)=O)(C)C.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([OH:25])[CH2:23][CH3:24])=[CH:18][CH:17]=1.[C:26]1(O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH3:24])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1072901-(4-Bromophenyl)propan-1-ol

Product 1

HCID 69118208HCID 69118208, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Azodicarboxylic acid diisopropyl ester (2.8 g, 14.0 mmol) was added to the mixture of 1-(4-bromophenyl)propan-1-ol (2.0 g, 9.3 mmol), phenol (1.05 g, 11.2 mmol), triphenylphosphine (3.7 g, 14.0 mmol) and tetrahydrofuran (40 mL) at room temperature. Then the mixture was stirred at room temperature for 12 hours. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give 1-bromo-4-(1-phenoxypropyl)benzene as a colorless oil (2.0 g, 4%). 1H NMR (300 MHz, CDCl3): δ 7.44 (d, J=8.4 Hz, 2H), 7.25-7.15 (m, 4H), 6.89-6.80 (m, 3H), 4.98 (t, J=6.5 Hz, 1H), 2.00-1.72 (m, 2H), 0.99 (t, J=7.5 Hz, 3H).

Workup

  1. concentrationThe resultant mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-3ce5b5846d054b46965a804057bb8eb5
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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