Aluminum(III) Chloride → HCID 66607562, compound

HRID 221103Notes

Reaction equation

HRID 221103 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=1)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-]>C(OCC)C>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 63796624HCID 63796624, compound

Product 1

HCID 66607562HCID 66607562, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the above 3-bromo-2-thienyl-4-ethylphenylmethanol (12.4 g) in diethyl ether (10 ml) was added dropwise into a suspension of lithium aluminum hydride (2.6 g) and aluminum chloride (9.0 g) in diethyl ether (35 ml) at 0° C. Subsequently, the mixture was stirred at room temperature overnight, and then poured onto ice. The mixture was extracted with diethyl ether, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane) to give 3-bromo-2-(4-ethylphenylmethyl)thiophene (8.77 g) as colorless oil. APCI-Mass m/Z 279/281 (M+H).

Workup

  1. additionpoured onto ice
  2. extractionThe mixture was extracted with diethyl ether
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-33b6bde0cb7747268ad06008af465d26
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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