Potassium Bromide → HCID 9974424, compound

HRID 1795492Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:24]C)=[C:4]([O:22]C)[CH:5]=[C:6]([CH:8]=[CH:9][C:10]2[CH:15]=[C:14]([O:16]C)[C:13]([O:18]C)=[C:12]([O:20]C)[CH:11]=2)[CH:7]=1.Cl.N1C=CC=CC=1.[K+].[Br-]>>[Br:1][C:2]1[C:3]([OH:24])=[C:4]([OH:22])[CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[C:14]([OH:16])[C:13]([OH:18])=[C:12]([OH:20])[CH:11]=2)[CH:7]=1

Participants

Reactant 3

HCID 253877Potassium Bromide

HCID 10176127Pyridinium chloride

HCID 69588658HCID 69588658, compound

Product 1

HCID 9974424HCID 9974424, compound

Procedure

Demethylation: The 1-(5-bromo-3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethylene (1.3 g) on demethylation with pyridine hydrochloride (7 g) under the conditions noted in example 1 gave 2, m.p. 148° C.; IR (KBr) νmax 3450, 1610, 1536, 1461, 1431, 1340, 1291, 1191, 1038, 997, 954, 842, 799 cm−1; 1H NMR (DMSO-d6, 400 MHz) δ 9.81 (1H, s), 9.21 (1H, s), 8.88 (2H, s), 8.30 (1H, s), 7.13 (1H, s), 6.93 (1H, s), 6.72 (1H, d, J=16.2 Hz), 6.64 (1H, d, J=16.2 Hz), 6.47 (2H, s).

Workup

customgave 2, m.p. 148° C.

Sources & evidence

ORD record: ord-445215a5fc524be6a4195ddc5cbbc190
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026518B2

Reaction notes

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