Trifluoroacetic acid → HCID 66672636, compound

HRID 2384962Notes

Reaction equation

HRID 2384962 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[O:30])=[C:4]([OH:32])[CH:3]=1.FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[O:30])=[C:4]([OH:32])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66672888HCID 66672888, compound

Product 1

HCID 66672636HCID 66672636, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Procedure

To an ice cold stirred solution of 3-(4-bromo-2-hydroxyphenyl)-1-(diphenylmethyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one (13.1 g, 27.1 mmol) in triethylsilane (25.0 mL) was added trifluoroacetic acid (25.0 mL). The solution was stirred at ambient temperature for 64 h, then concentrated in vacuo to dryness. Recrystallization from diethyl ether (25.0 mL) in a Branson ultrasonic bench top water bath afforded 3-(4-bromo-2-hydroxyphenyl)-1-(diphenylmethyl)-1,3-dihydro-2H-indol-2-one (10.1 g, 79%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ9.17 (s, 1H), 7.40-7.03 (m, 13H), 6.99-6.92 (m, 2H), 6.79-6.74 (m, 2H), 6.58-6.50 (m, 1H), 5.10 (s, 1H); MS (ES−) m/z 468.2 (M−1), 470.2 (M−1).

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. customRecrystallization from diethyl ether (25.0 mL) in a Branson ultrasonic bench top water bath

Sources & evidence

ORD record
ord-cadb0e28a6e1418fad10b2e6eb4195c9
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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