1,2-Dibromo-1,1,2,2-tetrafluoroethane → HCID 18398751, compound

HRID 1018915Notes

Reaction equation

HRID 1018915 reaction equation
C([Li])(C)(C)C.[C:6]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[Br:31]C(F)(F)C(F)(F)Br>CCCCC.CCOCC>[C:6]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)=[C:14]1[Br:31])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 18398754HCID 18398754, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18398751HCID 18398751, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

tert-Butyllithium (28.1 ml of a 1.7 mol solution in pentane) was added slowly to a stirred solution of 1-tert-butoxycarbonyl-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole (15.0 g) in dry ether at −78° C. under a dry nitrogen atmosphere. During the addition the temperature was maintained below −65° C. The reaction was stirred at −78° C. for 45 min at which time 1,2-dibromotetrafluoroethane (6.24 ml) was added. The reaction mixture was then allowed to warm to room temperature over 18 h, after which time it was quenched with water (100 ml) and extracted into ether (250 ml). The organic layer was separated, washed with water (250 ml) and brine (250 ml), dried over MgSO4, filtered and the solvent removed under reduced pressure to give an orange oil. Purification by flash chromatography (SiO2; n-hexane/ethyl acetate 10:1) afforded the product as a pale yellow oil (7.12 g); 1H (250 MHz, CDCl3) δ1.50-2.00 (6H, br m), 1.61 (9H, s), 3.05 (2H, t, J=7.5 Hz), 3.43 (1H, m), 3.56 (1H, m), 3.74 (1H, m), 3.91 (1H, m), 4.61 (1H, t, J=2.5 Hz), 7.26 (2H, m), 7.54 (1H, d, J=5.0 Hz) and 8.07 (1H, d, J=5.0 Hz).

Workup

  1. additionDuring the addition the temperature
  2. temperaturewas maintained below −65° C
  3. additionwas added
  4. customafter which time it was quenched with water (100 ml)
  5. extractionextracted into ether (250 ml)
  6. customThe organic layer was separated
  7. washwashed with water (250 ml) and brine (250 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure
  11. customto give an orange oil
  12. customPurification by flash chromatography (SiO2; n-hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-036dec8298134a258b488bd6e42693e4
Source dataset
uspto-grants-2002_11
Patent number
US06486153B1

Reaction notes

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