Triphenylphosphine → 1-[(2-Bromo-5-methoxybenzyl)oxy]-6-methoxynaphthalene

HRID 2086123Notes

Reaction equation

HRID 2086123 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.[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([Br:24])=[C:20]([CH:23]=1)[CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:24][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:23][C: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 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10867706(2-Bromo-5-methoxyphenyl)methanolHCID 110084166-Methoxynaphthalen-1-ol

Product 1

HCID 121253081-[(2-Bromo-5-methoxybenzyl)oxy]-6-methoxynaphthaleneYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-methoxynaphthol (12.9 g, 74.1 mmol), 5-methoxy-2-bromobenzyl alcohol (17.7 g, 81.6 mmol), and triphenylphosphine (31.1 g, 119 mmol) in THF (400 mL) was slowly added a solution of DEAD (20.6 g, 119 mmol) in THF (50 mL). The solution was stirred overnight, concentrated onto silica, and purified by silica column (10% ethyl acetate—hexanes) to yield 16.38 g (59%) of the title compound as a white solid: mp 83-84° C.; 1H NMR (CDCl3): δ 3.78 (3H, s), 3.92 (3H, s), 5.25 (2H, s), 6.75-6.77 (2H, m), 7.12 (1H, d, J=2.44 Hz), 7.15 (1H, dd, J=2.44 Hz, J=9.28 Hz), 7.24 (1H, d, J=2.93 Hz), 7.32-7.36 (2H, m), 7.48 (1H, d, J=8.79 Hz), 8.27 (1H, d, J=9.23 Hz); MS (ESI) m/z373/375 ([M+H]+);

Workup

  1. concentrationconcentrated onto silica
  2. custompurified by silica column (10% ethyl acetate—hexanes)

Sources & evidence

ORD record
ord-580a6b323efd40f196e29ad9c7ef6717
Source dataset
uspto-grants-2004_04
Patent number
US06723747B2

Reaction notes

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