4-Bromoaniline → HCID 70911894, compound

HRID 918814Notes

Reaction equation

HRID 918814 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([Br:12])=[CH:14][CH:15]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 78074-BromoanilineHCID 12070Methyl 3-bromobenzoate

Product 1

HCID 70911894HCID 70911894, compound

Procedure

Reaction of methyl 3-bromobenzoate with 4-bromoaniline according to general procedure A provided methyl ester of Compound 9 as a green oil (46% yield). 1H NMR (CDCl3, 500 MHz): δ=7.71 (s, 1H), 7.61 (d, J=7.7 Hz, 1H), 7.38 (d, J=8.6 Hz, 2H), 7.34 (t, J=7.9 Hz, 1H), 7.23 (d, J=8.1 Hz, 1H), 6.96 (d, J=8.7 Hz, 2H), 5.81 (s, 1H), 3.91 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=167.2, 143.1, 141.9, 132.6, 131.7, 129.7, 122.6, 122.1, 119.9, 118.8, 113.8, 52.4.

Sources & evidence

ORD record
ord-ab7711aeafde4b52a0c3069d96debea4
Source dataset
uspto-grants-2016_03
Patent number
US09271961B2

Reaction notes

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