Chloroform → HCID 59714931, compound

HRID 2223852Notes

Reaction equation

HRID 2223852 reaction equation
[CH:1]1([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18]O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40].C(Cl)(Cl)Cl>ClCCl>[Br:40][CH2:18][CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:8](=[O:9])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59715021HCID 59715021, compound

Product 1

HCID 59714931HCID 59714931, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclohexyl-N-[2-(2-hydroxyethyl)phenyl]acetamide (780 mg) in dichloromethane (20 mL) were added triphenylphosphine (938 mg) and carbon tetrabromide (1.12 g) at room teperature. The solution was stirred at room temperature for 1 hour. Chloroform was added and the solution was washed in turn with water and saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=7:3) to give the title compound (450 mg).

Workup

  1. washthe solution was washed in turn with water and saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-e03ca1b071774215b1231d6aa236766b
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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