Potassium Hydroxide → [2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-acetic acid

HRID 1873152Notes

Reaction equation

HRID 1873152 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:15]=[C:14]([C:16]2[C:25]3[C:26]4[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=4[S:28][C:24]=3[C:23]([Br:33])=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[CH:21]3)[CH:13]=[C:12]([Br:34])[C:5]=1[O:6][CH2:7][C:8]([O:10]C)=[O:9]>C1COCC1.CO.O>[Br:3][C:4]1[CH:15]=[C:14]([C:16]2[C:25]3[C:26]4[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=4[S:28][C:24]=3[C:23]([Br:33])=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[CH:21]3)[CH:13]=[C:12]([Br:34])[C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 10794136[2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-acetic acid, methyl ester

Product 1

HCID 10675368[2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-acetic acidYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 N Aqueous potassium hydroxide (2.66 mL, 2.66 mmol) was added to a stirred suspension of [2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl )-phenoxy]-acetic acid, methyl ester (1.51 g, 2.37 mmol) in THF (13 mL) and methanol (4 mL). Dissolution occurred. After 2.5 h at ambient temperature, the reaction mixture was diluted with water and extracted with ether (100 mL). The aqueous phase was acidified with 10% aqueous HCl and filtered. The solid was washed with water and triturated with pet. ether. The solid was dried in vacuo at 70° C. to provide the title compound as a white solid (1.34 g, 91%): mp 259-261° C.: NMR (DMSO-d6): δ8.29 (dd, J=8, 1 Hz, 1 H), 8.06 (dd, J=8, 1 Hz, 1 H), 7.82 (s, 2 H), 7.79 (ddd, J=8, 6, 2 Hz, 1 H), 7.61 (m, 2 H), 7.52 (ddd, J=8, 7, 1 Hz, 1 H), 7.32 (ddd, J=8, 7, 1 Hz, 1 H), 6.73 (dd, J=8, 1 Hz, 1 H), 4.78 (s, 2 H); MS (EI): [M+], 3 bronine isotope pattern, 618 (30%), 620 (90%) 622 (100%) 624 (50%); Anal. Calc. for C24H13Br3O3S: C, 46.41, H, 2.11, N, 0.00. Found: C, 46.38, H, 1.99, N, 0.01.

Workup

  1. dissolutionDissolution
  2. extractionextracted with ether (100 mL)
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. customtriturated with pet. ether
  6. customThe solid was dried in vacuo at 70° C.

Sources & evidence

ORD record
ord-ad9c0ad77546439a9a27b90962774bd6
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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