Trifluoroacetic acid → HCID 86684904, compound

HRID 2402895Notes

Reaction equation

HRID 2402895 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[SH:9].FC(F)(F)C(O)=O.[C:17]1([C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][C:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6457Triphenylcarbinol2×HCID 5194462-Chloro-4-fluorothiophenol

Product 1

HCID 86684904HCID 86684904, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4-fluoro-benzenethiol (250 g, 1.54 mol) was dissolved in dichloromethane (1.25 L) and trifluoroacetic acid (120 mL, 1.57 mol) followed by triphenylmethanol (400 g, 1.54 mol) were added at room temperature (ice bath cooling necessary during addition of triphenylmethanol). The mixture was stirred for 1.5 h at room temperature, concentrated and dried in vacuo to yield the title compound as a yellow solid (622 g, 99% purity by HPLC, 99%), that was used without further purification in the next step. 1H NMR (CDCl3, 400 MHz): δ 6.55 (ddd, J=2.9 Hz, 8.0 Hz, 8.9 Hz, 1H), 6.91 (dd, J=6.2 Hz, 8.9 Hz, 1H), 6.97 (dd, J=2.9 Hz, 8.6 Hz, 1H), 7.20-7.27 (m, 9H), 7.34-7.39 (m, 6H).

Workup

  1. additionwere added at room temperature
  2. concentrationconcentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-bf472721fe7749d7834af2c2649c6ea5
Source dataset
uspto-grants-2014_08
Patent number
US08796471B2

Reaction notes

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