Water → Methanesulfonic acid 4-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl Ester

HRID 1873138Notes

Reaction equation

HRID 1873138 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]1[C:14]2[C:13]3[C:15]([C:23]4[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=4)=[C:16]4[C:21](=[CH:22][C:12]=3[S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH:20]=[CH:19][CH:18]=[CH:17]4.O>C(Cl)Cl.N1C=CC=CC=1>[CH:6]1[C:14]2[C:13]3[C:15]([C:23]4[CH:24]=[CH:25][C:26]([O:29][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:27][CH:28]=4)=[C:16]4[C:21](=[CH:22][C:12]=3[S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH:20]=[CH:19][CH:18]=[CH:17]4

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 107823884-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenol

Product 1

HCID 15481262Methanesulfonic acid 4-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl EsterYield 114.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Methylsulfonyl chloride (0.63 mL, 8.14 mmol) was added dropwise to a cold (ice bath) solution of 4-benzo[b]naphtho[2,3-d]thiophen-11-yl-phenol (2.00 g, 5.43 mmol) in dry methylene chloride (10 mL) and pyridine (2.08 mL). After stiring at ambient temperature for ca. 36 h. the reaction mixture was combined with water (100 mL). The organics were extracted with ether (100 mL), washed with 10% HCl (100 mL) and concentrated to give the title compound as a white solid (2.51 g, 100%); mp 136-139° C.; NMR (CDCl3); δ 8.38 (s, 1H), 7.97-7.95 (m, 1H), 7.80-7.78 (m, 1H), 7.60-7.50 (m, 6H), 7.43-7.35 (m, 2H), 7.07 (ddd, J=8, 7, 1 Hz, 1H), 6.68 (d, J=8 Hz, 1H), 3.33 (s, 3H); MS (EI): [M+] 404 (100%); Anal. calc. for C23H16O3S2+0.07 C6H14, C, 68.52, H, 4.17, N, 0.03. Found: C, 67.91, H, 3.85, N, 0.06.

Workup

  1. extractionThe organics were extracted with ether (100 mL)
  2. washwashed with 10% HCl (100 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b686ebcf78ea47feb572e819daca3c88
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

Loading…