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

HRID 1873152ノート

反応式

HRID 1873152 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-ad9c0ad77546439a9a27b90962774bd6
出典データセット
uspto-grants-2000_08
特許番号
US06110962

反応ノート

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