N-bromobutanimide → 7-amino-4-bromo-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372506Notes

Reaction equation

HRID 1372506 reaction equation
[NH2:1][C:2]1[C:14]([Cl:15])=[C:13]2[C:5]([C:6]3[C:11]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:20])[CH:7]=3)=[CH:4][C:3]=1[F:21].[Br:22]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[C:14]([Cl:15])=[C:13]2[C:5]([C:6]3[C:11]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:20])[C:7]=3[Br:22])=[CH:4][C:3]=1[F:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 210720137-amino-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 102217817-amino-4-bromo-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-oneYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-amino-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (1.36 g, 4.42 mmol) in anhydrous CH2Cl2 (13 mL) was cooled in an ice bath, placed under a nitrogen atmosphere, treated with N-bromosuccinimide (0.787 g, 4.42 mmol) and stirred at 0–5° C. for one hour. The reaction mixture was filtered through a pad of silica gel and the pad was washed with EtOAc. The filtrate and washings were evaporated under vacuum. The residue was purified by flash chromatography on a Biotage 40M column using 10:1 hexanes-EtOAc as eluting solvent. The product containing fractions were evaporated under vacuum to afford 7-amino-4-bromo-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (1.08 g, 63%) as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washthe pad was washed with EtOAc
  3. customThe filtrate and washings were evaporated under vacuum
  4. customThe residue was purified by flash chromatography on a Biotage 40M column
  5. washas eluting solvent
  6. additionThe product containing fractions
  7. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-eaf69e33e4d74b7db39c98816f32b172
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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