Cesium carbonate → 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromide

HRID 1841864Notes

Reaction equation

HRID 1841864 reaction equation
[Br:1][CH2:2][C:3]([O:5][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH3:7])=[O:4].[I-].[OH:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([S+:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]3[CH:33]=[CH:34][CH:35]=[CH:36][C:25]2=3)=[CH:19][C:18]=1[CH3:37].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Br-:1].[CH3:37][C:18]1[CH:19]=[C:20]([S+:24]2[C:25]3[CH:36]=[CH:35][CH:34]=[CH:33][C:26]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=3)[CH:21]=[C:22]([CH3:23])[C:17]=1[O:16][CH2:2][C:3](=[O:4])[O:5][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 538027202-Phenylpropan-2-yl 2-bromoacetateHCID 867124735-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium iodide

Product 1

HCID 867124715-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromideYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-phenylpropan-2-yl 2-bromoacetate (1.96 g, 7.63 mmol) was added to a solution of 5-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium iodide (3.00 g, 6.94 mmol) and cesium carbonate (2.94 g, 9.02 mmol) in DMF (40 mL) at 0° C., warmed to r.t. and stirred overnight. The reaction mixture was diluted with water (200 mL) and washed with DCM (3×200 mL). The organic layers were washed with water (3×300 mL), concentrate and poured onto MTBE. The precipitate was filtered and dried to afford the title compound (3.80 g, 97%) as a white solid. 1H NMR (300 MHz, ((CD3)2SO) δ: 8.52 (d, J=7.5 Hz, 2H), 8.33 (d, J=7.5 Hz, 2H), 7.96 (t, J=7.2 Hz, 2H), 7.5 (d, J=7.9 Hz, 2H), 7.20-7.39 (m, 5H), 4.61 (s, 2H), 2.19 (s, 6H), 1.71 (s, 6H).

Workup

  1. washwashed with DCM (3×200 mL)
  2. washThe organic layers were washed with water (3×300 mL)
  3. concentrationconcentrate
  4. additionpoured onto MTBE
  5. filtrationThe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-99ac94529cc049eb9cccb22df5b988f1
Source dataset
uspto-grants-2015_02
Patent number
US08945814B2

Reaction notes

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