Boron tribromide → 6-(4-Hydroxy-phenyl)-1-methyl-naphthalen-2-ol

HRID 1830636Notes

Reaction equation

HRID 1830636 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[CH3:21].B(Br)(Br)Br>>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4]([CH3:21])=[C:3]([OH:2])[CH:12]=[CH:11]3)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 114031912-Methoxy-6-(4-methoxyphenyl)-1-methylnaphthalene

Product 1

HCID 103080756-(4-Hydroxy-phenyl)-1-methyl-naphthalen-2-ol

Procedure

The title compound was prepared by reacting 2-methoxy-6-(4-methoxyphenyl)-1-methylnaphthalene (0.35 g, 1.26 mmol) with boron tribromide 3.8 mL of 1 N solution, 3.8 mmol) according to method D to yield 0.15 g (48%) of a white solid: mp>170° C. (dec.); 1H NMR (DMSO-d6): δ 2.42 (3H, s), 6.87 (2H,k d, J=8.33 Hz), 7.15 (1H, d, J=8.81 Hz), 7.59 (2H, d, J=8.35 Hz), 7.65 (1H; d, J=8.93 Hz), 7.71 (1H, dd, J=1.24 Hz, J=8.90 Hz), 7.88 (1H, d, J=8.87 Hz), 7.95 (1H, s), 9.49 (1H, s), 9.52 (1H, s); MS (ESI) 249 m/z (M−H)−.

Sources & evidence

ORD record
ord-fd4018a5871e4cc28687798f684a80c3
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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