Sodium Sulfide → HCID 86692645, compound

HRID 1470830Notes

Reaction equation

HRID 1470830 reaction equation
[Br:1][C:2]1[C:6]([CH2:7]Cl)=[C:5]([CH2:9]Cl)[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[S-2:15].[Na+].[Na+]>CO>[Br:1][C:2]1[C:6]2[CH2:7][S:15][CH2:9][C:5]=2[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 86692646HCID 86692646, compound

Product 1

HCID 86692645HCID 86692645, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Compound (3) from the previous step was dissolved into 500 ml slightly boiling methanol, and a solution of sodium sulfide in 500 ml methanol was added drop-wise over about 1 hour at boiling temperature. The reactant was then kept at boiling temperature for about 1 hour. Methanol was removed by rotary evaporation and the sticky residue was absorbed by silica gel. The purification of product was performed by column chromatography using petroleum ether/ethyl acetate (30:1) as the eluent. Methyl 3-bromo-4,6-dihydrothieno[3,4-b]thiophene-2-carboxylate was obtained as colorless oil. The yield was about 75%.

Workup

  1. customfor about 1 hour
  2. customMethanol was removed by rotary evaporation
  3. customthe sticky residue was absorbed by silica gel
  4. customThe purification of product

Sources & evidence

ORD record
ord-ae6e1c04e9394dceb7506b803d511a6c
Source dataset
uspto-grants-2015_04
Patent number
US09006568B2

Reaction notes

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