Boron tribromide → HCID 10286186, compound

HRID 895199Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][C:13]=3[CH3:20])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:21].B(Br)(Br)Br>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=3[CH3:20])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11483402HCID 11483402, compound

Product 1

HCID 10286186HCID 10286186, compound

Procedure

The title compound was prepared by reacting 1-chloro-6-(4-methoxy-2-methylphenyl)-2-naphthol (400 mg, 1.41 mmol) with boron tribromide (4.0 mL of 1.0 M solution in CH2Cl2, 4.0 mmol) according to method D to yield 310 mg (77%) of a yellowish solid: mp 216-218° C.; 1H NMR (DMDO-d6): δ 2.20 (1H, s), 6.68 (1H, dd, J=8.19 Hz, J=2.42 Hz), 6.72 (1H, d, J=2.13 Hz), 7.10 (1H, d, J=8.16 Hz), 7.29 (1H, d, J=8.89 Hz), 7.29 (1H, d, J=8.89 Hz), 7.53 (1H, dd, J=8.78 Hz, J=1.62 Hz), 7.76 (1H, d, J=1.38 Hz), 7.80 (1H, d, J=8.94 Hz), 8.02 (1H, d, J=8.72 Hz), 9.4 (1H, s), 10.43 (1H, s); 13 NMR (DMDO-d6): δ 20.47, 112.20, 112.99, 117.00, 118.66, 121.85, 127.83, 128.09, 128.38, 129.47, 130.00, 130.88, 131.65, 136.09, 136.51, 150.88, 156.62; MS (ESI) m/z283/285(M−H)−.

Sources & evidence

ORD record: ord-0220b1cef3b343f883054b8980dd9b06
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

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