Trifluoroacetic acid → 6-bromospiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 422850Notes

Reaction equation

HRID 422850 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:31][O:32][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10](C(C1C=CC=CC=1)C1C=CC=CC=1)[C:9]3=[O:30].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:31][O:32][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH:10][C:9]3=[O:30]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 461941846-bromo-1'-(diphenylmethyl)spiro[1-benzofuran-3,3'-indol]-2'(1H)-one

Product 1

HCID 461940506-bromospiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 89.4%

Procedure

A stirred solution of 6-bromo-1′-(diphenylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1H)-one (2.5 g, 5.2 mmol), triethylsilane (5.0 mL) and trifluoroacetic acid (15.0 mL) was refluxed for 14 h. The solution was concentrated in vacuo and precipitated from hexanes to afford 6-bromospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.47 g, 89%) as a colorless solid: MS (ES+) m/z 316.1 (M+1), 318.1 (M+1).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customprecipitated from hexanes

Sources & evidence

ORD record
ord-45d94972ab204039bf0e80ef8d456cec
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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