Iodine → HCID 68935963, compound

HRID 1437533Notes

Reaction equation

HRID 1437533 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[C:3]=1[NH2:4].C(=O)(O)[O-].[Na+].[I:20]I>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[NH:4][CH:14]1[CH:9]2[CH2:10][CH2:11][CH2:12][CH:13]1[I:20]

Participants

5

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 68934421HCID 68934421, compound

Product 1

HCID 68935963HCID 68935963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the 2-bromo-6-cyclohex-2-en-1-ylaniline mixture (0.85 g, 3.4 mmol) above in dichloromethane (50 mL) was added sodium bicarbonate (2.3 g, 27 mmol) followed by iodine (3.5 g, 14 mmol). The reaction was stirred for 3 hours and then diluted with dichloromethane (100 mL). The organic phase was washed with a 10% w/w aqueous solution of sodium thiosulfate, washed with brine, and was dried by passing through a hydrophobic frit. The organic solution was concentrated to leave crude 8-bromo-1-iodo-2,3,4,4a,9,9a-hexahydro-1H-carbazole. MS m/z 378, 380 (M+1).

Workup

  1. washThe organic phase was washed with a 10% w/w aqueous solution of sodium thiosulfate
  2. washwashed with brine
  3. customwas dried
  4. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-9449ae0343a84d63bf36d7a2aff8f709
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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