Formaldehyde → HCID 67155707, compound

HRID 452451Notes

Reaction equation

HRID 452451 reaction equation
[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[C:13]1([B:19]([OH:21])O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:22](O)(=O)CC.C=O>C1(C)C=CC=CC=1>[C:13]1([B:19]2[O:21][CH2:22][C:7]3[CH:8]=[CH:9][C:4]([S:3][C:2]([F:11])([F:1])[F:12])=[CH:5][C:6]=3[O:10]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 1032Propionic Acid2×HCID 66827Phenylboronic AcidHCID 27778923-(Trifluoromethylthio)phenol

Product 1

HCID 67155707HCID 67155707, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-[(trifluoromethyl)thio]phenol (10.0 g, 51.5 mmol), phenylboronic acid (6.91 g, 56.7 mmol), propionic acid (1.92 ml, 25.8 mmol) and paraformaldehyde (1.46 g, 48.7 mmol), and toluene was heated at reflux using a Dean-Stark trap to separate water formed during the reaction. Additional paraformaldehyde was added (3×1 g+7×0.5 g, 0.22 mol) and additional propionic acid was added (2×0.5 ml, 13.4 mmol). The mixture was brought to ambient temperature, quenched with water and extracted with EtOAc. The combined organic layers were washed with Na2CO3 (10%), dried (Na2SO4), filtered and evaporated to dryness (14.0 g). MS m/z (rel. intensity, 70 eV) 310 (M+, 41), 309 (19), 242 (11), 241 (bp), 240 (28), 109 (14).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customto separate water
  4. customformed during the reaction
  5. additionwas added (2×0.5 ml, 13.4 mmol)
  6. customwas brought to ambient temperature
  7. customquenched with water
  8. extractionextracted with EtOAc
  9. washThe combined organic layers were washed with Na2CO3 (10%)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated to dryness (14.0 g)

Sources & evidence

ORD record
ord-b2f4091410a74214b26f5e1940dff236
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

Loading…