3-Chloro-2,6-difluorobenzaldehyde → 1-(3-Chloro-2,6-difluorophenyl)-2-methylprop-2-en-1-ol

HRID 1481296Notes

Reaction equation

HRID 1481296 reaction equation
[CH2:1]=[C:2]([Mg]Br)[CH3:3].[Cl:6][C:7]1[C:8]([F:16])=[C:9]([C:12]([F:15])=[CH:13][CH:14]=1)[CH:10]=[O:11]>C1COCC1>[Cl:6][C:7]1[C:8]([F:16])=[C:9]([CH:10]([OH:11])[C:2]([CH3:3])=[CH2:1])[C:12]([F:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7363383-Chloro-2,6-difluorobenzaldehydeHCID 178456138HCID 178456138, compound

Product 1

HCID 1182360651-(3-Chloro-2,6-difluorophenyl)-2-methylprop-2-en-1-olYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of prop-1-en-2-ylmagnesium bromide (0.5M in THF) (2 mL, 1.000 mmol) was added 3-chloro-2,6-difluorobenzaldehyde (136 mg, 0.769 mmol) in THF (1 mL) dropwise at 0° C. under Ar and stirred at 0° C. for 15 mins. The reaction mixture was quenched with sat. aq.NH4Cl and extracted with ether. The organic phase was washed with sat. aq.NH4Cl and brine, dried over MgSO4, filtered, and concentrated. Purification by flash chromatography to yield 73A as colorless oil (87 mg, 52%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.36-7.28 (m, 1H), 6.91-6.83 (m, 1H), 5.48 (d, J=9.2 Hz, 1H), 5.12-5.06 (m, 1H), 5.04-4.99 (m, 1H), 2.56 (dt, J=9.2, 2.2 Hz, 1H), 1.75 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with sat. aq
  2. extractionNH4Cl and extracted with ether
  3. washThe organic phase was washed with sat. aq
  4. dry with materialNH4Cl and brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-46e77794eac649339a554e6295ca6f66
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

Loading…