1,2-Dibromo-1,1,2,2-tetrafluoroethane → HCID 66684882, compound

HRID 579169Notes

Reaction equation

HRID 579169 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1.[Li]CCCC.[Br:20]C(F)(F)C(Br)(F)F>C1COCC1>[Br:20][C:7]1[CH:6]=[C:5]([C:4]#[C:3][C:2]([CH3:14])([CH3:13])[CH3:1])[S:9][C:8]=1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 581140725-(3,3-Dimethyl-but-1-ynyl)-thiophene-2-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 66684882HCID 66684882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a of solution of 5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid (6.5 g, 31.3 mmol, 1.0 equiv) in THF (150 mL) at −78° C. was added n-BuLi (44.9 mL, 1.6 M in heptane, 71.9 mmol, 2.3 equiv) and the resulting solution was stirred at −78° C. for 1 hour. To the solution was then added 1,2-dibromo-1,1,2,2-tetrafluoro-ethane (16.2 g, 62.5 mmol, 2.0 equiv) and the solution was allowed to warm to room temperature over 2 hours. The reaction was quenched by addition of sat. aq. NH4Cl solution and the mixture was extracted with EtOAc. The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated. The crude material was continued to the next step with no further purification.

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. customThe reaction was quenched by addition of sat. aq. NH4Cl solution
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude material was continued to the next step with no further purification

Sources & evidence

ORD record
ord-1f9d8a1126914acc96736366e446cbe0
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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