1-Bromo-3-chloropropane → HCID 57675746, compound

HRID 2264682Notes

Reaction equation

HRID 2264682 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.Br[CH2:19][CH2:20][CH2:21][Cl:22].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:22][CH2:21][CH2:20][CH2:19][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 576757604-(2-Methylindol-1-yl)phenol

Product 1

HCID 57675746HCID 57675746, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-(2-Methylindol-1-yl)phenol (0.36 mmol) was heated at 70° C. in 2-butanone (3 mL) with 1-bromo-3-chloropropane (0.107 mL, 1.08 mmol) and potassium carbonate (0.15 g, 1.08 mmol) overnight. The solvent was evaporated. The resulting residue was diluted with ethyl acetate and washed with saturated ammonium chloride solution. The aqueous layer was back-extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. SiO2 chromatography with 5-20% ethyl acetate/hexanes gave the desired product as a colorless oil, 60 mg (56% yield, 2 steps). LC-MS (C18H18ClNO calc'd 299) m/z 300, 302 (M+H).

Workup

  1. customThe solvent was evaporated
  2. additionThe resulting residue was diluted with ethyl acetate
  3. washwashed with saturated ammonium chloride solution
  4. extractionThe aqueous layer was back-extracted with ethyl acetate
  5. dry with materialThe organic extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5c40e5b6b7314b5ba4f8a093f1d5fa33
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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