Toluene → HCID 20291281, compound

HRID 1413945Notes

Reaction equation

HRID 1413945 reaction equation
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[Cl:30][C:31]([F:39])([F:38])[C:32]([C:34]([F:37])([F:36])[Cl:35])=[O:33]>O>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([C:32]([C:31]([Cl:30])([F:39])[F:38])([C:34]([Cl:35])([F:37])[F:36])[OH:33])=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 313762-Propanone, 1,3-dichloro-1,1,3,3-tetrafluoro-2×HCID 12151496HCID 12151496, compound

Product 1

HCID 20291281HCID 20291281, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.5 g (0.05 mole) of 1-benzhydryl-indoline, 100 ml of toluene, 2 ml of water, and 10.9 g (0.055 mole) of 1,3-dichlorotetrafluoroacetone is refluxed for 3 hrs. Another 10.9 g portion of 1,3-dichlorotetrafluoroacetone is added, and refluxing is continued for 13 hrs. The moisture is then removed azeotropically, and the solvent is evaporated to give a crude, viscous residue of 1-benzhydryl-α,α-bis(chlorodifluoromethyl)-2,3-dihydro-1H-indole-5-methanol. This crude material is tedious to purify and is more conveniently used without further purification for conversion to the desired product.

Workup

  1. temperatureis refluxed for 3 hrs
  2. temperaturerefluxing
  3. customThe moisture is then removed azeotropically
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-7c1024c6b72740cd98862ddf12d97fb3
Source dataset
uspto-grants-1981_02
Patent number
US04251659

Reaction notes

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