Carbon tetrabromide → HCID 21186736, compound

HRID 1384283Notes

Reaction equation

HRID 1384283 reaction equation
O[CH2:2][CH:3]1[C:9]2=[N:10][C:11]([CH3:19])=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:13]=[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[Br:40][CH2:2][CH:3]1[C:9]2=[N:10][C:11]([CH3:19])=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:13]=[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 21186712HCID 21186712, compound

Product 1

HCID 21186736HCID 21186736, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In an atmosphere of argon, ethyl 9-hydroxymethyl-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (263.0 mg, 1.00 mmol) was dissolved in methylene chloride (5.0 ml), the solution was mixed with triphenylphosphine (393.0 mg, 1.50 mmol) at 0° C. and then with carbon tetrabromide (663.3 mg, 2.00 mmol) and the mixture was stirred at room temperature for 3 hours. The reaction solution was mixed with saturated sodium bicarbonate aqueous solution and water and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine. After drying with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:5) to obtain the title compound (349.1 mg, quantitative) as white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe resulting organic layer was washed with water and saturated brine
  3. dry with materialAfter drying with anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=1:5)

Sources & evidence

ORD record
ord-09284aefc8214fb891086815664b3dcb
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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