Bromine → 5'-Bromo-1',2'-dihydrospiro[cyclohexane-1,3'-indole]-2'-one

HRID 444737Notes

Reaction equation

HRID 444737 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:2]1=[O:15].C([O-])(=O)C.[Na+].[Br:21]Br>C(O)(=O)C>[Br:21][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:15])[C:3]12[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 12888301Spiro[cyclohexane-1,3'-indolin]-2'-one

Product 1

HCID 114714965'-Bromo-1',2'-dihydrospiro[cyclohexane-1,3'-indole]-2'-oneYield 654.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of spiro[cyclohexane-1,3′-[3H]indol]-2′-(1′H)-one (17.6 g, 9 mmol) in acetic acid (300 mL) was added sodium acetate (8.0 g, 0.1 mol) and bromine (14.6 g, 91 mmol) with stirring. After 30 minutes at room temperature, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted twice with EtOAc. The combined organic layers were washed with water, dried (MgSO4) and evaporated and the residue was triturated with hexane. The precipitate was collected, and dried in vacuo to obtain 5′-bromospiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (16.5 g, 67%) as off-white crystals: mp 196-199° C.; 1H NMR (DMSO-d6): δ 1.62 (m, 10H), 6.8 (d, 1H, J=6.8 Hz), 7.36 (d, 1H, J=8.2, 1.8 Hz), 7.58 (dd, 1H, J=8.2, 1.8 Hz), 10.44 (s, 1H).

Workup

  1. customthe reaction mixture was partitioned between water and EtOAc
  2. extractionThe aqueous phase was extracted twice with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe residue was triturated with hexane
  7. customThe precipitate was collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-edec224428f64978bbb7d68d8fcc79d8
Source dataset
uspto-grants-2013_07
Patent number
US08476262B2

Reaction notes

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