Sulfuryl chloride → HCID 10183002, compound

HRID 1069213Notes

Reaction equation

HRID 1069213 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.S(Cl)([Cl:30])(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:11]2[S:12][C:13]([CH2:16][Cl:30])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 12972353HCID 12972353, compound

Product 1

HCID 10183002HCID 10183002, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (ice bath) solution of acetic acid 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester (4.00 g, 9.4 mmol) in anhydrous methylene chloride (41 mL) was added sulfuryl chloride (0.76 mL, 10.3 mmol) dropwise over a period of 10 minutes. After stirring 1 hour in the ice bath the reaction was quenched with water (100 mL) and diluted with diethyl ether. After filtering, the layers were separated. Silica gel was added to the organic layer and the solvents were removed. The adsorbate was flash chromatographed (gradient 90/10-80/20 petroleum ether/ethyl acetate) to give the title compound as a white solid (2.57 g, 59%): NMR (DMSO-d6); δ8.23 (d, J=8 Hz, 1H), 7.71 (dd, J=8,1 Hz, 1H), 7.55-7.43 (m, 4H), 7.33-7.30 (m, 2H), 5.09 (s, 2H), 2.34 (s, 3H), 1.66 (s, 3H).

Workup

  1. customwas quenched with water (100 mL)
  2. additiondiluted with diethyl ether
  3. filtrationAfter filtering
  4. customthe layers were separated
  5. additionSilica gel was added to the organic layer
  6. customthe solvents were removed
  7. customchromatographed (gradient 90/10-80/20 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-c91f367138df4eee844e51e7c7ea6731
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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