Bromine → HCID 68958558, compound

HRID 269387Notes

Reaction equation

HRID 269387 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=[C:13]2[O:24][CH3:25].CC([O-])=O.[K+].[Br:31]Br>CC(O)=O.O>[Br:31][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][C:2]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:22])([F:21])[F:23])[CH:14]=[C:13]2[O:24][CH3:25]

Participants

6

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 68960321HCID 68960321, compound

Product 1

HCID 68958558HCID 68958558, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of 6-(1-benzofuran-2-yl)-4-methoxy-2-(trifluoromethyl)quinoline (0.930 g, 2.71 mmol) in HOAc (30 mL) at 0° C. was added KOAc (0.319 g, 3.25 mmol). The reaction was stirred at this temperature for 10 minutes, and then a solution of Br2 (0.154 mL, 2.98 mmol) in HOAc (5 mL) was added dropwise to it over a period of ˜10 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 2.5 hours. The reaction mixture was then diluted with H2O (10 mL). The solid that formed was filtered off and washed with excess H2O and hexane. This solid was then recrystallized from EtOAc:hexane to afford the product (0.750 g, 66%) as a solid. Mass spectrum (+ESI, [M+H]+) m/z 422/424. 1H NMR (500 MHz, DMSO-d6): δ 8.95 (s, 1H), 8.65 (d, 1H, J=8.9 Hz), 8.29 (d, 1H, J=8.9 Hz), 7.80 (d, 1H, J=8.1 Hz), 7.66 (d, 1H, J=8.1 Hz), 7.36-7.58 (m, 3H), and 4.26 ppm (s, 3H).

Workup

  1. stirringstirred for 2.5 hours
  2. customThe solid that formed
  3. filtrationwas filtered off
  4. washwashed with excess H2O and hexane
  5. customThis solid was then recrystallized from EtOAc

Sources & evidence

ORD record
ord-caf369c0d0cd456aac6ed2fbc849ad51
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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