Boron tribromide → HCID 11601927, compound

HRID 1830686Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:20])[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:21]C.B(Br)(Br)Br>>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:20])[C:8]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 22048158HCID 22048158, compound

Product 1

HCID 11601927HCID 11601927, compound

Procedure

The title compound was prepared by reacting 1,5-dichloro-2-methoxy-6-(4-methoxyphenyl)naphthalene (0.15 g, 0.45 mmol) with boron tribromide (1.4 mL of 1N solution) according to method D to yield 0.10 g (73%) of a white solid: mp 204–206° C.; 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.47 Hz), 7.33 (2H, d, J=8.45 Hz), 7.46 (1H, d, J=9.26 Hz), 7.56 (1H, d, J=8.80 Hz), 8.06 (1H, d, J=8.81 Hz), 8.17 (1H, d, J=9.28 Hz), 9.68 (1H, bs), 10.84 (1H, bs); MS (ESI) m/z 303/305/307(M−H)−.

Sources & evidence

ORD record: ord-a89abac046ae449b88b020d37f05b3e6
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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