Toluene → 1-(4'-Fluorophenyl)-1,3-DihydroIsobenzofuran-5-Carbonitrile

HRID 1596799Notes

Reaction equation

HRID 1596799 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)O)=[C:5]([CH2:18][OH:19])[CH:4]=1)#[N:2].C1(C)C=CC=CC=1>OP(O)(O)=O>[F:17][C:14]1[CH:13]=[CH:12][C:11]([CH:9]2[C:6]3[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[CH2:18][O:19]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 99213624-[(4-Fluorophenyl)hydroxymethyl]-3-(hydroxymethyl)benzenecarbonitrile

Product 1

HCID 98561591-(4'-Fluorophenyl)-1,3-DihydroIsobenzofuran-5-Carbonitrile

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
80 °C

Procedure

Crude (4-cyano-2-hydroxymethylphenyl)(4-fluorophenyl)methanol (700 g) is dissolved in H3PO4 (60%, 3000 mL) and the solution is heated to 80° C. for 3 hours. Toluene (1000 mL) is added and the phases are separated. The aqueous phase is further extracted with toluene (1000 mL). The toluene phases are joined and the solvents are removed in vacuo. The remaining crystals are recrystallized from EtOH (99%). Yield 219 g (29%). DSC onset: 97° C.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is further extracted with toluene (1000 mL)
  3. customthe solvents are removed in vacuo
  4. customThe remaining crystals are recrystallized from EtOH (99%)
  5. custom97° C.

Sources & evidence

ORD record
ord-efab58fc1589432da33e20c4b40dfda8
Source dataset
uspto-grants-2001_09
Patent number
US06291689B1

Reaction notes

Loading…