Bromine → HCID 13563091, compound

HRID 637315Notes

Reaction equation

HRID 637315 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]32[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]3)=[CH:4][CH:3]=1.C[Si](N([Si](C)(C)C)C(=[O:27])C(F)(F)F)(C)C.BrBr>C(Cl)CCl>[OH:27][CH:6]1[C:5]2[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[C:8]2([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]2)[CH2:7]1

Participants

5

Reactant 3

HCID 24408BromineHCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 15572728HCID 15572728, compound

Product 1

HCID 13563091HCID 13563091, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6'-Fluoro-spiro[imidazolidine-4,1'-indan]-2,5-dione, (C.A. reg. no. 66892-38-4)(1.1 g, 5 mmol) was combined with 2.65 ml (10 mmol) bis-(trimethylsilyl) trifluoroacetamide, 0.8 g (5 mmol) bromine and 30 ml ethylene dichloride and heated at reflux for 2.5 hours. During this time color was lost from the reaction mixture. The reaction mixture was concentrated in vacuo to an amber oil which was diluted with 10 ml water. Over a period of 16 hours at 25° C. a solid gradually formed. This material was isolated by filtration and dried in vacuo at 100° C. to give 1.0 g (85% yield) of the title compound: mp 209°-211° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo to an amber oil which
  4. additionwas diluted with 10 ml water
  5. customOver a period of 16 hours at 25° C. a solid gradually formed
  6. customThis material was isolated by filtration
  7. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-8256adf3af23489c8ef80f708be2f2f5
Source dataset
uspto-grants-1985_12
Patent number
US04556670

Reaction notes

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