N-bromobutanimide → HCID 23130396, compound

HRID 2080125Notes

Reaction equation

HRID 2080125 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[S:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:18][C:12]1[S:11][C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[CH:9][C:8]=1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 23130354HCID 23130354, compound

Product 1

HCID 23130396HCID 23130396, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Phenoxy-thiophen-2-yl)-[1,3]dioxolane described in Preparation Example 109 (4.88 g, 19.7 mmol) and N-bromosuccinimide (3.85 g, 21.7 mmol) were dissolved in tetrahydrofuran (100 mL), and the solution was stirred for 4.5 hours at room temperature. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the residue was silica gel-filtered to obtain 2-(5-bromo-4-phenoxy-thiophen-2-yl)-[1,3]dioxolane (5.48 g) as a pale yellow oil.

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. filtrationfiltered

Sources & evidence

ORD record
ord-eb291baff53141238b8e1f627c318647
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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