Water → HCID 59263302, compound

HRID 644085Notes

Reaction equation

HRID 644085 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:9]=1)[C:5]#[N:6].[OH2:21].[C:22]1([CH3:28])C=CC=C[CH:23]=1.CN([CH:32]=[O:33])C>>[CH3:32][O:33][CH2:23][C@H:22]([CH3:28])[O:21][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6228DimethylformamideHCID 592633063-Fluoro-5-[4-(methanesulfonyl)phenoxy]benzonitrile

Product 1

HCID 59263302HCID 59263302, compound

Conditions

Temperature
70 °C

Procedure

3-Fluoro-5-(4-methanesulfonyl-phenoxy)-benzonitrile (22.31 mmol; 6.50 g) was dissolved in dry DMF (32.5 ml) and this was added to the flask containing the anion of S-1-methoxyproapan-2-ol. The mixture was heated to 70° C. and held at 70° C. for 18 hrs. Water (20 ml) was added, then sufficient toluene to dissolve the precipitated solid was added. The mixture was extracted further with toluene (3×100 ml) and the combined toluene extract was washed with water (3×200 ml). The toluene layers were distilled down to low volume in vacuo and iso-hexane was added (50 ml). The resulting precipitate of the desired product was filtered off, washed with iso-hexane (2×25 ml) and dried in a vacuum oven at 40° C. overnight (6.0 g, 74.4% yield).

Workup

  1. additionthis was added to the flask
  2. additioncontaining the anion of S-1-methoxyproapan-2-ol
  3. additionwas added
  4. extractionThe mixture was extracted further with toluene (3×100 ml)
  5. extractionthe combined toluene extract
  6. washwas washed with water (3×200 ml)
  7. distillationThe toluene layers were distilled down to low volume in vacuo and iso-hexane
  8. additionwas added (50 ml)
  9. filtrationThe resulting precipitate of the desired product was filtered off
  10. washwashed with iso-hexane (2×25 ml)
  11. customdried in a vacuum oven at 40° C. overnight (6.0 g, 74.4% yield)

Sources & evidence

ORD record
ord-9bdd5a57061540409c6d49aca0017e97
Source dataset
uspto-grants-2010_04
Patent number
US07700640B2

Reaction notes

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