Boron tribromide → HCID 23045756, compound

HRID 2108232Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:18]C)=[C:11]([O:16]C)[CH:12]=2)[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([OH:18])=[C:11]([OH:16])[CH:12]=2)[CH:7]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To 17.0 g (0.061 mole) of 2-(4-chlorobutyl)-6,7-dimethoxynaphthalene in 350 mL of methylene chloride cooled at -70° C. under an argon atmosphere was added 122 mL (0.122 mole) of 1M boron tribromide in methylene chloride, dropwise over 30 minutes. The reaction mixture was stirred for 30 minutes at -70° C. and then kept at -20° C. for 17 hours. Workup as in Example 7 gave 2-(4-chlorobutyl)-6,7-dihydroxynaphthalene as a colorless solid (15.3g). This solid, 21.8g (0.18 mole) of benzyl bromide and 25.3g (0.18 mole) of potassium carbonate in 300 mL of acetone was stirred at reflux for 18 hours. Workup as in Example 7 and purification of the crude product by HPLC using 5% ethyl acetate-hexane gave a solid which was recrystallized from ether-hexane, to give 13.0 g (49% yield), mp 54°-59 °, of 2-(4-chlorobutyl)-6,7-bis(phenylmethoxy)-naphthalene.

Workup

waitkept at -20° C. for 17 hours

Sources & evidence

ORD record: ord-074c945c5104494ebbe0ed409c03c31f
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04937371

Reaction notes

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