Boron tribromide → HCID 10192794, compound

HRID 895211Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]3)=[C:5]([CH3:20])[CH:4]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]3)=[C:5]([CH3:20])[CH:4]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11459740HCID 11459740, compound

Product 1

HCID 10192794HCID 10192794, compound

Procedure

The title compound was prepared by reacting 6-(4-methoxy-2-methylphenyl)-2-naphthol (420 mg, 1.59 mmol) with boron tribromide (4.53 mL of 1.0 M solution in CH2Cl2, 4.53 mmol) according to method D to yield 400 mg (quantitative yield) of a yellowish solid: mp 191-193° C.; 1H NMR (DMDO-d6): δ 6.68 (1H, dd, J=8.41 Hz, J=2.21 Hz), 6.72 (1H, d, J=2.21 Hz), 7.07-7.11 (2H, m), 7.14 (1H, d, J=2.21 Hz), 7.33 (1H, dd, J=8.41 Hz, J=2.21 Hz), 7.64 (1H, d, J=0.885 Hz), 7.68 (1H, d, J=8.41 Hz), 7.77 (1H, d, J=9.29 Hz), 9.33 (1H, s), 9.69 (1H, s); 13C NMR (DMDO-d6): δ 108.34, 112.82, 116.84, 118.68, 125.47, 127.13, 127.56, 128.02, 129.26, 130.71, 132.26, 133.02, 135.63, 135.90, 155.11, 156.31; MS (ESI) m/z 249 (M−H)+.

Sources & evidence

ORD record: ord-07cd2a98f355435ba0c5845f7d1566f0
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

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