Boron tribromide → HCID 58978553, compound

HRID 1180339Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 58978545HCID 58978545, compound

Product 1

HCID 58978553HCID 58978553, compound

Procedure

The title compound was prepared by reacting 3-chloro-3′-fluoro-4′-methoxy-1,1′-biphenyl-4-carbaldehyde (990 mg, 3.75 mmol) with boron tribromide (11.25 mL of 1 N solution in methylene chloride, 11.25 mmol) according to Method F to yield 940 mg (100%) of yellowish solid. The compound was used in the next step without purification. The analytical sample was obtained by HPLC purification: mp 206-208° C.; 1H NMR (DMSO-d6): δ 7.06 (1H, t, J=8.79 Hz), 7.51-7.53 (1H, m), 7.71 (1H, dd, J=2.47 Hz, J=12.63 Hz), 7.81-7.83 (1H, m), 7.89 (1H, d, J=7.96 Hz), 7.91 (1H, d, J=1.66 Hz), 10.329(1H, s), 10.330 (1H, s); IR 1667 cm−1; MS (ESI) m/z 249/251 (M−H)−.

Sources & evidence

ORD record: ord-4f38fd9b618a4b53b7435bbd4327de9b
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279600B2

Reaction notes

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