Water → 4-bromo-2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

HRID 1627329Notes

Reaction equation

HRID 1627329 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[CH2:4][S:5][C:6]1[N:7]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)([CH3:13])[CH3:12])=[CH:9][N:10]=1.C(=O)([O-])[O-].[Na+].[Na+].O.[Br:41]Br>C(Cl)Cl>[Br:41][C:9]1[N:10]=[C:6]([S:5][CH2:4][C:3]2[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:2]=2[Cl:1])[N:7]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:8]=1[C:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24408BromineHCID 469086492-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

Product 1

HCID 866622414-bromo-2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazoleYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (950 mg, 1.81 mmol) and sodium carbonate (634 mg, 5.98 mmol) in DCM:H2O (5 mL:5 mL) was added bromine (0.1 mL, 2.00 mmol) dropwise at 0° C. The resulting mixture was stirred for 3 h and diluted with DCM (15 mL). The organic layer was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The crude material was purified with flash chromatography to afford the title compound (970 mg, 89%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.62 (s, 6H), 4.35 (s, 2H), 6.43 (m, 2H), 6.80 (t, 2H), 6.84 (dd, 1H), 6.95 (t, 1H), 6.99 (dd, 1H), 7.16 (m, 2H), 7.25 (t, 1H); MS (EI) m/z 602 [M+H]+.

Workup

  1. washThe organic layer was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified with flash chromatography

Sources & evidence

ORD record
ord-bad940ed5b6e4017b958e7b0c4db23d7
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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