Bromine → 5-Bromo-8-methoxy-2-methylquinoline

HRID 1423099Notes

Reaction equation

HRID 1423099 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[CH:8]2.[Br:14]Br>>[Br:14][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11]2

Participants

3

Reactant 2

HCID 24408BromineHCID 3169868-Methoxy-2-Methylquinoline

Product 1

HCID 47150215-Bromo-8-methoxy-2-methylquinolineYield 86.6%

Procedure

Prepared using the same procedure described in Example 78 from 8-methoxy-2-methyl-quinoline [CAS 3033-80-5] (1.21 g, 6.96 mmol) and bromine (1.35 g, 8.42 mmol) to afford titled compound as a yellow solid (1.52 g, 86%). 1H NMR (DMSO-d6) 8.30 (d. J=8.4, 1H), 7.76 (d. J=8.4, 1H), 7.57 (d. J=8.4, 1H), 7.10 (d. J=8.4, 1H), 3.93 (s, 3H), 2.66 (s, 3H). LC/MS (Method B) 2.07 min, [M+1]+ 252/254.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-15c5ba5ce5f6423d89f4724d1be164f8
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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