Triphenylphosphine → Methyl 3-chloro-4-(1,3-difluoropropan-2-yloxy)benzoate

HRID 515752Notes

Reaction equation

HRID 515752 reaction equation
[F:1][CH2:2][CH:3]([OH:6])[CH2:4][F:5].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1O)[C:11]([O:13][CH3:14])=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[O:6][CH:3]([CH2:4][F:5])[CH2:2][F:1])[C:11]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 679851,3-Difluoro-2-propanolHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 67248585Methyl 3-chloro-4-(1,3-difluoropropan-2-yloxy)benzoateYield 131.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3-difluoropropan-2-ol (2.57 g, 26.8 mmol) in THF (35 mL) was added methyl 3-chloro-4-hydroxybenzoate (2.00 g, 10.72 mmol), followed by triphenylphosphine (7.03 g, 26.8 mmol) and DIAD (5.21 mL, 26.8 mmol). The reaction was stirred overnight at room temperature, diluted with EtOAc and washed with brine. The organics were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography to give the title compound (3.743 g) as a clear oil. LCMS m/z=265.1 [M+H]+.

Workup

  1. washwashed with brine
  2. customThe organics were separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9ed069f600d349998924b808e3b82e77
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

Loading…