Benzyl Bromide → HCID 86622266, compound

HRID 1395877Notes

Reaction equation

HRID 1395877 reaction equation
[F:1][C:2]([F:28])([C:5]([F:27])([F:26])[C:6]([F:25])([F:24])[C:7]([F:23])([F:22])[C:8]([F:21])([F:20])[C:9]([F:19])([F:18])[C:10]([F:17])([F:16])[C:11]([F:15])([F:14])[CH2:12][OH:13])[CH2:3][OH:4].[OH-].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH2:31]([O:13][CH2:12][C:11]([F:15])([F:14])[C:10]([F:16])([F:17])[C:9]([F:18])([F:19])[C:8]([F:20])([F:21])[C:7]([F:22])([F:23])[C:6]([F:25])([F:24])[C:5]([F:26])([F:27])[C:2]([F:28])([F:1])[CH2:3][OH:4])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 27334041H,1H,10H,10H-Perfluorodecane-1,10-diol

Product 1

HCID 86622266HCID 86622266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dry 5 mL round bottom flask was charged with 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecane-1,10-diol (2.2 mmol, 1.0 g), dry DMF (2.5 mL), and crushed potassium hydroxide (2.2 mmol, 121 mg). The mixture was flushed with argon and benzyl bromide (0.7 mmol, 123 mg) was added dropwise over 15 minutes. The solution was allowed to stir overnight at room temperature under argon. The reaction mixture was concentrated in vacuo, and the residue was partitioned between aqueous saturated ammonium chloride and ethyl acetate. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, washed with water then brine, dried over MgSO4, and concentrated in vacuo. The residue was purified via flash column chromatography on silica gel using 5% EtOAc in petroleum ether as the eluent. The product was isolated as colorless oil; upon drying under high vacuum for 12 h, the oil solidified (90%). 1H NMR (CDCl3): δ7.36 (m, 5H), 4.68 (s, 2H), 4.10 (td, 2H, J=14, 6), 3.94 (t, 2H, J=14), 1.96 (t, 1H, J=7); 13C NMR (CDCl3): δ136.6, 128.8, 128.5, 128.0, 74.7, 66.9, 60.9; 19F NMR (CDCl3): δ −119.8, −122.3, −122.8, −123.7, −123.9.

Workup

  1. additionwas added dropwise over 15 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between aqueous saturated ammonium chloride and ethyl acetate
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. washwashed with water
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash column chromatography on silica gel using 5% EtOAc in petroleum ether as the eluent
  9. customThe product was isolated as colorless oil
  10. customupon drying under high vacuum for 12 h

Sources & evidence

ORD record
ord-d1c73ab6e7074e48b13b11e620cbccc0
Source dataset
uspto-grants-2014_12
Patent number
US08900562B2

Reaction notes

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