Boron tribromide → HCID 10308197, compound

HRID 1830650Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11346659HCID 11346659, compound

Product 1

HCID 10308197HCID 10308197, compound

Procedure

The title compound was prepared by reacting 3-chloro-4-(6-methoxy-2-naphthyl)phenol (2.4 g, 8.43 mmol) with boron tribromide (21.9 mL of 1.0 M solution in CH2Cl2, 21.9 mmol) according to method D to yield 2.1 g (92%) of a yellowish solid: mp 209–210° C.; 1H NMR (DMDO-d6): δ 6.86 (1H, dd, J=8.42 Hz, J=2.45 Hz), 6.97 (1H, d, 2.41 Hz), 7.11 (1H, dd, J=8.78 Hz, J=2.35 Hz), 7.16 (1H, d, J=2.15 Hz), 7.30 (1H, d, J=8.40 Hz), 7.42 (1H, dd, J=8.51 Hz, J=1.71 Hz), 7.71 (1H, d, J=8.59 Hz), 7.76 (1H, s), 7.80 (1H, d, J=8.82 Hz), 9.82 (1H, s), 10.01 (1H,s); 13C NMR (DMDO-d6): δ 108.45, 114.79, 116.21, 118.90, 125.53, 127.43, 127.77, 127.92, 129.56, 130.70, 131.73, 132.34, 133.18, 133.52, 155.56, 157.46; MS (ESI) m/z 269/271 (M−H)−.

Sources & evidence

ORD record: ord-147002edb5af4d2895f55395bcf602c3
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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