Water → HCID 22972914, compound

HRID 589251Notes

Reaction equation

HRID 589251 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.Cl[C:12]([CH3:15])([CH3:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl>[C:12]([C:5]1[S:1][C:2]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)=[CH:3][CH:4]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10486tert-BUTYL CHLORIDEHCID 681202,2'-BithiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22972914HCID 22972914, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2′-bithiophene (10 g, 60.1 mmol) was dissolved in DCM (300 mL) and 2-chloro-2-methylpropane (7.95 g, 72.2 mmol) was added. Aluminum chloride (8.82 g, 66.2 mmol) was added in one portion, and the colourless solution turned a green/brown colour immediately. The reaction mixture was stirred at room temperature for 30 minutes, then was poured into water (500 mL), mixed well and separated. The aqueous portion was extracted with DCM (200 mL) and the combined organics were washed with brine (2×400 mL), dried over MgSO4, filtered and solvent removed by rotary evaporation to afford a clear, green oil (13.3 g, 99%) that was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.17 (dd, J=5.1, 1.1 Hz, 1H), 7.10 (dd, J=3.6, 1.1 Hz, 1H), (dd, J=5.1, 3.6 Hz, 1H), 6.98 (d, J=3.6 Hz, 1H), 6.73 (d, J=3.7 Hz, 1H), 1.40 (s, 9H).

Workup

  1. additionmixed well
  2. customseparated
  3. extractionThe aqueous portion was extracted with DCM (200 mL)
  4. washthe combined organics were washed with brine (2×400 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent removed by rotary evaporation

Sources & evidence

ORD record
ord-9352cc2a110545baa2dbf92937b075f7
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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