Phosphorus tribromide → 10-Bromomethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline

HRID 1993754Notes

Reaction equation

HRID 1993754 reaction equation
O[CH2:2][C:3]1[C:4]2[CH2:5][C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:16])[NH:8][C:7]=3[C:17]=2[CH:18]=[CH:19][CH:20]=1.P(Br)(Br)[Br:22]>C1COCC1>[Br:22][CH2:2][C:3]1[C:4]2[CH2:5][C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:16])[NH:8][C:7]=3[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1611877910-(hydroxymethyl)-6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-one

Product 1

HCID 8661101310-Bromomethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinolineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Fine powder of Compound (I)(25) (10-hydroxymethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline, 7.3 g, 27.7 mmol) was suspended in THF (150 mL). A solution of PBr3 (83 mL, 1M in dichloromethane) was added dropwise at room temperature. After the complete addition, the resultant mixture was stirred overnight and quenched by addition of water (150 mL). The suspension was stirred for 1 hour and filtered. The resultant solid was washed with water (2×100 mL) and ethyl acetate (2×100 mL) and dried in a vacuum oven to provide 10-Bromomethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline in 81% yield. 1H NMR spectrum (in DMSO-d6): δ 12.31 (s, 1H); 8.23 d, J=7.5 Hz, 1H); 7.95 (m, 1H); 7.75 (m, 2H); 7.45 (m, 2H); 4.87 (s, 2H); 3.97 (s, 2H).

Workup

  1. additionAfter the complete addition
  2. customquenched by addition of water (150 mL)
  3. filtrationfiltered
  4. washThe resultant solid was washed with water (2×100 mL) and ethyl acetate (2×100 mL)
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-fa877a99019f42e181aff054b1e40522
Source dataset
uspto-grants-2010_01
Patent number
US07652028B2

Reaction notes

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