Potassium Carbonate → HCID 86650354, compound

HRID 468689Notes

Reaction equation

HRID 468689 reaction equation
[CH2:1](Br)[C:2]#[C:3][CH3:4].[F:6][CH:7]([F:18])[O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[O:8][CH:7]([F:6])[F:18])[CH:13]=[O:14])[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

Product 1

HCID 86650354HCID 86650354, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

But-2-ynyl bromide (0.29 mL, 3.4 mmol) was added to a suspension of 4-difluoromethoxy-3-hydroxybenzaldehyde (0.43 g, 2.3 mmol) and potassium carbonate (0.95 g, 6.9 mmol) in acetonitrile (5 mL). The suspension was heated to reflux for 16 h and then concentrated under reduced pressure. Water was added and the aqueous phase was extracted with EtOAc. The combined organic fractions were washed with water, brine, dried. The product was concentrated under reduced pressure providing 3-(but-2-ynyloxy)-4-difluoromethoxybenzaldehyde (0.53 g, 97%) as a yellow crystalline solid; mp 46-47° C.; δH (500 MHz, CDCl3) 1.86 (t, J=2.5 Hz, 3H, C≡CCH3), 4.81 (q, J=2.5 Hz, 2H, OCH2), 6.68 (t, J=72.0 Hz, 1H, CHF2), 7.33 (d, J5,6=8.0 Hz, 1H, H5), 7.50 (dd, J5,6=8.0, J2,6=2.0 Hz, 1H, H6), 7.63 (d, J2,6=2.0 Hz, 1H, H2), 9.96 (s, 1H, CHO); δC (125 MHz, CDCl3) 3.7, 57.5, 72.7, 85.3, 113.4, 115.6 (t, J=256 Hz), 121.8, 125.1, 134.4, 145.3, 149.7, 190.7; νmax 1123, 1268, 1435, 1505, 1597, 1698, 2858 cm−1.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added
  5. extractionthe aqueous phase was extracted with EtOAc
  6. washThe combined organic fractions were washed with water, brine
  7. customdried
  8. concentrationThe product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-419a05a7cdd542268099b4e891e5961e
Source dataset
uspto-grants-2014_01
Patent number
US08624056B2

Reaction notes

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