Lithium Bromide → HCID 52948299, compound

HRID 877515Notes

Reaction equation

HRID 877515 reaction equation
[Br:1][C:2]1(Br)[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:16])=[C:9]([Cl:15])[CH:10]=3)[NH:5][C:4]=2[C:3]1=[O:17].[Li+].[Br-]>CN(C=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:16])=[C:9]([Cl:15])[CH:10]=3)[NH:5][C:4]=2[C:3]=1[OH:17]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 67377648HCID 67377648, compound

Product 1

HCID 52948299HCID 52948299, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

2,2-Dibromo-6,7-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.1 g, 0.24 mmol) was dissolved in DMF (2 mL) and LiBr (0.02 g, 0.26 mmol) followed by Li2CO3 (0.01 g, 0.25 mmol) were added. The reaction mixture was heated to 110° C. for 2 h, cooled to room temperature and quenched with saturated NH4Cl (10 mL), extracted with EtOAc (2×15 mL) and the combined organic extracts were concentrated in vacuo to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant] to provide the title compound as light red solid (30 mg, 37%). 1H NMR (500 MHz, CDCl3, δ in ppm): 8.28 (bs, 1H), 8.07 (s, 1H), 7.57 (s, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.31 (d, J=8.5 Hz, 1H), 5.72 (s, 1H).

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. customquenched with saturated NH4Cl (10 mL)
  4. extractionextracted with EtOAc (2×15 mL)
  5. concentrationthe combined organic extracts were concentrated in vacuo
  6. customto give the crude compound which
  7. customwas purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-e85ace3eec03421886aca8f2b1dd8336
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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