1,1-Dibromoethane → HCID 12044735, compound

HRID 1057607Notes

Reaction equation

HRID 1057607 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:28][CH:29](Br)[CH3:30]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:30][CH2:29][Br:28])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 112011,1-Dibromoethane2×HCID 11430Potassium CarbonateHCID 113693279-Benzyl-9H-carbazol-4-ol

Product 1

HCID 12044735HCID 12044735, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 9-benzyl-9H-Carbazol-4-ol (2.46 g, 9.00 mmol), potassium carbonate (5.11 g, 27.0 mmol), and DMF (10 mL) is added dibromoethane (3.90 mL, 45.0 mmol). The mixture is stirred at 80° C. for 4.5 h and then allowed to cool and stir the remainder of the night. The mixture is then stirred at 85° C.; after about 2 h an additional 1.0 mL of dibromoethane is added. After 5.5 h the mixture is cooled and the solvent and excess dibromoethane are removed in vacuo. The residue is partitioned between Et2O, water, and brine. The organic layers are dried over MgSO4 and taken to dryness. Chromatography on silica gel (250 mL) using EtOAc-heptane (10/90 to 20/80) to give 1.80 g (53%) after crystallization from CH2Cl2-hexane; IR (drift) 1583, 1458, 1446, 1342, 1333, 1281, 1270, 1245, 1154, 1147, 1114, 783, 753, 734, 719 cm−1; 1H NMR (CDCl3) δ3.87, 4.58, 5.51, 6.66, 7.02, 7.12, 7.2-7.4, 8.43. Anal. Calcd for C21H18BrNO: C, 66.33; H, 4.77; N, 3.68; Br, 21.01. Found: C, 66.30; H, 4.76; N, 3.62.

Workup

  1. temperatureto cool
  2. stirringstir the remainder of the night
  3. stirringThe mixture is then stirred at 85° C.
  4. temperatureAfter 5.5 h the mixture is cooled
  5. customthe solvent and excess dibromoethane are removed in vacuo
  6. customThe residue is partitioned between Et2O, water, and brine
  7. dry with materialThe organic layers are dried over MgSO4
  8. customto give 1.80 g (53%)
  9. customafter crystallization from CH2Cl2-hexane

Sources & evidence

ORD record
ord-0e6736752582406f9408b457f1106410
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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