Water → HCID 23508114, compound

HRID 1883607Notes

Reaction equation

HRID 1883607 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]2[O:21][CH:20]3[CH:15]([CH2:16][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:19]3)[C:13]=2[CH:14]=1.[Br:29]N1C(=O)CCC1=O.O>CC(O)=O>[Br:29][C:11]1[C:12]2[O:21][CH:20]3[CH2:19][CH2:18][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16][CH:15]3[C:13]=2[CH:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 12125451HCID 12125451, compound

Product 1

HCID 23508114HCID 23508114, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

tert-Butyl 8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate (5.360 g, 12.750 mmol) was dissolved in 160 mL CH3COOH. N-Bromosuccinimide (4.539 g, 25.500 mmol) was added. The reaction mixture was stirred under N2 at rt for 27 h. The reaction mixture was poured into a mixture of 300 g ice and 100 mL water. The aqueous mixture was extracted with EtOAc (3×). The combined organic layers were washed with 5M NaOH (2×250 mL), 25% KOH (2×200 mL) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was chromatographed (SiO2, 15% EtOAc:hexane), and tert-butyl 6-bromo-8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate was obtained in 82% yield (5.250 g, 10.516 mmol). MS (ESI+) for C22H22BrCl2NO3 m/z 499.8 (M+H)+.

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc (3×)
  2. washThe combined organic layers were washed with 5M NaOH (2×250 mL), 25% KOH (2×200 mL) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was chromatographed (SiO2, 15% EtOAc:hexane)

Sources & evidence

ORD record
ord-6d9388f2987041f9a1c0a2ef90f4c39c
Source dataset
uspto-grants-2004_07
Patent number
US06762191B2

Reaction notes

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