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

HRID 1060033Notes

Reaction equation

HRID 1060033 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 67%

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, 0.09 mol) in acetic acid (300 cm3) was added sodium acetate (8.0 g, 0.1 mol) and bromine (14.6 g, 0.091 mol) with stirring. After 30 min. 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 the subtitled compound (1 6.5 g, 67%) as off-white crystals: mp 196-199° C.; 1H NMR (DMSO-d6) δ1.62 (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-a8ac958af8714a938cc98e306880e227
Source dataset
uspto-grants-2003_02
Patent number
US06521657B2

Reaction notes

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