Triethylamine → 4-Phenoxy-1-methyl-2-nitrobenzene

HRID 1371962Notes

Reaction equation

HRID 1371962 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].FC1C(OC)=C(F)C=C2C=1C=CN2C.CCN(CC)CC>C(Cl)Cl>[O:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:10])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 162713-Nitro-p-cresolHCID 66827Phenylboronic AcidHCID 210715554,6-Difluoro-5-methoxy-1-methyl-1H-indole

Product 1

HCID 210715624-Phenoxy-1-methyl-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine phenyl boronic acid (7.32 g, 60 mmol), 4-methyl-3-nitrophenol (4.5 g, 30 mmol), and Cu(oAC)2—H2O (6 g, 30 mmol) in 30 mL CH2Cl2 and treat with 6 g 4 A molecular sieves powder. Add Et3N (15.18 g, 150 mmol) dropwise, and stir the reaction at ambient temperature for 8 days. Dilute with 100 mL CH2Cl2 and filter through celite and concentrate to dryness. Purification by chromatography using 2% EtOAc in hexanes gave the desired product as a yellow oil.

Workup

  1. customthe reaction at ambient temperature for 8 days
  2. filtrationfilter through celite
  3. concentrationconcentrate to dryness
  4. customPurification by chromatography

Sources & evidence

ORD record
ord-f2a550f7062e42a5ad6d89d5e249d614
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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