Triphenylphosphine → HCID 69672908, compound

HRID 1751526Notes

Reaction equation

HRID 1751526 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[CH:8][CH:7]=[CH:6]2.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([I:23])=[C:19]([CH2:21]O)[CH:20]=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:14][C:15]1[CH:16]=[CH:17][C:18]([I:23])=[C:19]([CH:20]=1)[CH2:21][O:13][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 110084166-Methoxynaphthalen-1-olHCID 15339730(5-Bromo-2-iodophenyl)methanol

Product 1

HCID 69672908HCID 69672908, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methoxynaphthalen-1-ol (4.45 g, 25.6 mmol), (5-bromo-2-iodophenyl)methanol (8.0 g, 25.6 mmol) and triphenylphosphine (7.4 g, 28.2 mmol) in tetrahydrofuran (128 mL) at 0° C. was added diisopropyl azodicarboxylate (5.54 mL, 28.2 mmol). The reaction was allowed to warm to room temperature overnight. After 15 hours, more triphenylphosphine (1.3 g, 5 mmol) and diisopropyl azodicarboxylate (0.99 mL, 5 mmol) were added and the reaction was stirred at room temperature. After 24 hours, the reaction was concentrated and recrystallized from CH2Cl2 and hexanes to yield 1-(5-bromo-2-iodobenzyloxy)-6-methoxynaphthalene (7.82 g, 65%). The mother liquor was purified by flash column chromatography to yield more product (790 mg, 6.5%).

Workup

  1. waitAfter 24 hours
  2. concentrationthe reaction was concentrated
  3. customrecrystallized from CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-14e36dfd8be64d759166ea0b73e73205
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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