3-Bromobenzoic acid → 3-[2-(3,5-Dimethoxy-4-1-propylphenyl)ethenyl]benzoic acid

HRID 252313Notes

Reaction equation

HRID 252313 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH2:15])[CH:6]=[C:7]([O:12][CH3:13])[C:8]=1[CH2:9][CH2:10][CH3:11].Br[C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([OH:22])=[O:21].COC1C=C(C=CC2C=CC(C(O)=O)=CC=2)C=C(OC)C=1CCC>>[CH3:13][O:12][C:7]1[CH:6]=[C:5]([CH:14]=[CH:15][C:17]2[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=2)[C:20]([OH:22])=[O:21])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 114563-Bromobenzoic acidHCID 66842614(3,5-Dimethoxy-4-1-propylphenyl)etheneHCID 668426554-[2-(3,5-Dimethoxy-4-1-propylphenyl)ethenyl]benzoic acid

Product 1

HCID 668426583-[2-(3,5-Dimethoxy-4-1-propylphenyl)ethenyl]benzoic acidYield 77%

Procedure

This compound was synthesized from (3,5-dimethoxy-4-1-propylphenyl)-ethene and 3-bromobenzoic acid in 77% yield in the same way as described in preparation of 1B. 1HNMR (CDCl3, ppm): δ 1.32 (d, J=7.1 Hz, 6H), 3.63 (qint, J=7.1 Hz, 1H), 3.90 (s, 6H), 6.76 (s, 6H), 7.08 (d, J=17 Hz, 1H), 7.25 (d, J=17 Hz, 1H), 7.50 (t, J=7.7 Hz, 1H), 7.79 (d, J=7.7 Hz, 1H), 8.04 (d, J=7.7 Hz, 1H), 8.31 (s, 1H).

Sources & evidence

ORD record
ord-a4f5762808024d2b9b586352e038e7b7
Source dataset
uspto-grants-2011_01
Patent number
US07868047B2

Reaction notes

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