Benzyl Bromide → 3-(Benzyloxy)-1-bromonaphthalene

HRID 900150Notes

Reaction equation

[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[CH2:15]([O:12][C:4]1[CH:3]=[C:2]([Br:1])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Bromo-naphthalen-2-ol (5.0 g, 22.41 mmol) is dissolved in dry DMF (50 ml) under an atmosphere of argon. Sodium hydride (986 mg of a 60% suspension in mineral oil, 592 mg, 24.65 mmol) is added and the mixture is stirred at 50° C. for 1 h. After re-cooling to RT, benzyl bromide (3.46 ml, 4.98 g, 29.14 mmol) and tetrabutyl ammoniumiodide (828 mg, 2.24 mmol) are added. After 16 h at RT, the reaction mixture is diluted with EtOAc. The solution is washed twice with semi-concentrated brine (back extracted). The combined organic layers are dried over Na2SO4, the solvent is removed, and the residue is purified by FCC (hexane/EtOAc 100:0 to 95:5 to 90:10) to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 5.22 (s, 2H), 7.25 (d, J=1.5 Hz, 1H), 7.45 (m, 7H), 7.64 (d, J=2.4, 1H), 7.75 (d, J=7.8, 1H), 8.17 (d, J=7.8, 1H); ES-MS: 312 [M+H]+.

Workup

temperatureAfter re-cooling to RT
waitAfter 16 h at RT
washThe solution is washed twice with semi-concentrated brine (back extracted)
dry with materialThe combined organic layers are dried over Na2SO4
customthe solvent is removed
customthe residue is purified by FCC (hexane/EtOAc 100:0 to 95:5 to 90:10)

Sources & evidence

ORD record: ord-123c06e2ed224626bbe2c532cd988bb1
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358253B2

Reaction notes

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