Pentane → HCID 67128227, compound

HRID 2390590Notes

Reaction equation

HRID 2390590 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)=[CH:23][C:22]=1[CH2:35]O.[Br:37]C(Br)(Br)Br.CCCCC>ClCCl>[Br:37][CH2:35][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][C:21]=1[F:20])[CH2:27][O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1

Participants

6

Reactant 4

HCID 8003PentaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67128148HCID 67128148, compound

Product 1

HCID 67128227HCID 67128227, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4.44 g (16.94 mmol) triphenylphosphine in 10 ml dichloromethane is added in drops to an ice-cold solution of 3 g (12.49 mmol) [2-fluoro-5-(tetrahydropyrane-2-yloxymethyl)-phenyl]methanol and (15.61 mmol) tetrabromomethane in 30 ml anhydrous dichloromethane and stirred for another 45 minutes at 0° C. The reaction solution is mixed with pentane, the precipitation is suctioned off and washed with dichloromethane. The filtrate is washed with 5% sodium hydrogen carbonate solution, water and sodium chloride solution and dried over magnesium sulfate. After removing the solvent, the residue is purified by way of column chromatography on silica gel using diethyl ether/petrol ether 1:10.

Workup

  1. customthe precipitation
  2. washwashed with dichloromethane
  3. washThe filtrate is washed with 5% sodium hydrogen carbonate solution, water and sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customAfter removing the solvent
  6. customthe residue is purified by way of column chromatography on silica gel

Sources & evidence

ORD record
ord-c9605f343bba4505bea76a7462c33638
Source dataset
uspto-grants-2012_09
Patent number
US08273793B2

Reaction notes

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