Ammonium Chloride → HCID 10798147, compound

HRID 439879Notes

Reaction equation

HRID 439879 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[O:11][C:10]([CH:12]=[C:13](Br)Br)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[O:11][C:10]([C:12]#[CH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10570608HCID 10570608, compoundHCID 178418339Butyllithium

Product 1

HCID 10798147HCID 10798147, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred -78° C. solution in THF (200 mL) under argon of 2-[5-(4-fluorophenoxy)-2-furyl]-1,1-dibromoethene (23.1 g, 63.81 mmol), prepared as in step 2, was added n-butyl lithium (51.0 mL, 127.62 mmol, 2.5M in hexanes). The reaction was stirred for 0.5 hours at -78° C. Aqueous ammonium chloride was added to the cold reaction, the ice bath was removed and the reaction mixture allowed to warm to room temperature. The majority of THF was removed in vacuo. The resulting mixture was partitioned between water and ether. The combined ether layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (hexanes) to give 6.5 g (50%) of 2-[5-(4-fluorophenoxy)-2-furyl]-ethyne.

Workup

  1. customthe ice bath was removed
  2. temperatureto warm to room temperature
  3. customThe majority of THF was removed in vacuo
  4. customThe resulting mixture was partitioned between water and ether
  5. dry with materialThe combined ether layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (hexanes)

Sources & evidence

ORD record
ord-afeaf48bb2c94c0f82ff24ec2deeba5d
Source dataset
uspto-grants-1996_05
Patent number
US05516789

Reaction notes

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