Water → Methanesulfonic acid 4-(6-Chloro-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester

HRID 1873139Notes

Reaction equation

HRID 1873139 reaction equation
[CH:1]1[C:9]2[C:8]3[C:10]([C:18]4[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=4)=[C:11]4[C:16](=[CH:17][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4.S(Cl)([Cl:32])(=O)=O.O>C(Cl)(Cl)Cl>[Cl:32][C:17]1[C:7]2[S:6][C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:9]=3[C:8]=2[C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=2)=[C:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 15481262Methanesulfonic acid 4-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl Ester

Product 1

HCID 15481263Methanesulfonic acid 4-(6-Chloro-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl esterYield 88.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methanesulfonic acid 4-benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl ester (1.00 g, 2.47 mmol) in chloroform (10 mL) was added sulfuryl chloride (0.21 mL, 2.60 mmol, 1.05 eq) dropwise at room temperature under a dry nitrogen atmosphere. After stirring 19 hours the reaction mixture was added to water (100 mL) and the organics were extracted with ether (2×100 mL). The extracts were combined, washed with brine, combined with silica gel and the solvent was removed. The adsorbate was flash chromatrographed (85/15 petroleum ether/ethyl acetate) to give the title compound as a white solid (0.957 g, 88%): mp 155-158° C.; NMR (CDCl3); δ 8.41 (ddd, J=8, 1, 1 Hz, 1H), 7.82 (ddd, J=8, 1, 1 Hz, 1H), 7.67 (ddd, J=8, 7, 1 Hz, 1H), 7.61-7.56 (m, 3H), 7.51-7.45 (m, 3H), 7.42-7.38 (ddd, J=8, 7, 1 Hz, 1H), 7.10 (ddd, J=8, 7, 1 Hz, 1H), 6.64 (d, J=8 Hz, 1H), 3.34 (s, 3H); MS (+EI) : [M+], 1 chlorine isotope pattern, 438 (100%), 440 (40%); Anal. Calc. for C23H15ClO3S2: C, 62.93, H, 3.49, N, 0.00. Found: C, 62.72, H, 3.25, N, 0.03.

Workup

  1. extractionthe organics were extracted with ether (2×100 mL)
  2. washwashed with brine
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-5514aed8d1b444d8b390f2c7fdd87987
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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