Hydrochloric Acid → HCID 58913141, compound

HRID 1296688Notes

Reaction equation

HRID 1296688 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:31]=[CH:30][C:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[O:13][C:12](=[O:21])[C:11]=2[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])=[CH:7][CH:6]=1.[I:32]I.Cl>[NH4+].[OH-].CO.C(Cl)Cl>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:31]=[CH:30][C:8]([CH2:9][C:10]2[C:19]3[C:14](=[C:15]([I:32])[C:16]([OH:20])=[CH:17][CH:18]=3)[O:13][C:12](=[O:21])[C:11]=2[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 807IodineHCID 58913126HCID 58913126, compound

Product 1

HCID 58913141HCID 58913141, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of 4-(4-(2-Bromoethoxy)-benzyl)-3-(2,4-dichlorophenyl)-7-hydroxy-chromen-2-one (2.734 g, 5.26 mmol) in NH4OH (22 mL), MeOH (55 mL) and CH2Cl2 (33 mL) was added I2 (1.334 g, 5.26 mmol), and the resulting mixture was stirred at r.t for 30 min. Aqueous 4 M HCl was then added to lower the pH of the aqueous layer to 5. The resultant layers were separated and the aqueous phase was extracted with AcOEt (3×). The combined organic layers were washed with brine (2×), dried (MgSO4) and concentrated in vacuo. The residual beige solid (3.25 g, 96%) was used directly in the next step without further purification. 1H NMR (300 MHz, DMSO) δ 11.43 (s, 1H), 7.74 (d, J=2.0 Hz, 1H), 7.51–7.42 (m, 3H), 7.02 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.8 Hz, 1H), 6.78 (d, J=8.5 Hz, 2H), 4.21 (t, J=5.0 Hz, 2H), 4.04 (d, J=15.5 Hz, 1H), 3.73 (t, J=5.0 Hz, 2H), 3.70 (d, J=15.5 Hz, 1H); MS (ESI) m/z 642.7 (M−H)−; HPLC tR 7.27 min.

Workup

  1. customThe resultant layers were separated
  2. extractionthe aqueous phase was extracted with AcOEt (3×)
  3. washThe combined organic layers were washed with brine (2×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residual beige solid (3.25 g, 96%) was used directly in the next step without further purification

Sources & evidence

ORD record
ord-f10d4648ea31451aaa3e417f1fae92d4
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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