Boron tribromide → HCID 58998504, compound

HRID 1593043Notes

Reaction equation

HRID 1593043 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[O:22]C.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[OH:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58998396HCID 58998396, compound

Product 1

HCID 58998504HCID 58998504, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a chilled suspension of 7-Fluoro-6-methoxy-2-(4-nitrophenyl)-2H-isoquinolin-1-one (3.14 g, 10 mmol) in dichloromethane (50 mL) was added neat boron tribromide (8 mL, 85 mmol) via syringe. The brown suspension was stirred at room temperature for 24 hr. The solvent was decanted, washed with cold DCM, leaving a black residue, which was triturated on ice with methanol (80 mL). The solid was collected by filtration, then washed with water and dried to give 2.66 g (89%) of 7-Fluoro-6-hydroxy-2-(4-nitro-phenyl)-2H-isoquinolin-1-one. RP-HPLC: 3.93 min; ES-MS (M+H)+=301.0; 1H-NMR (DMSO-d6) δ (ppm): 6.66 (d,1), 7.16 (d, 1), 7.43 (d, 1); 7.76 (d, 2), 7.84 (d, 1), 8.33 (d, 2), 11.1 (br s, 1).

Workup

  1. customThe solvent was decanted
  2. washwashed with cold DCM
  3. customleaving a black residue, which
  4. customwas triturated on ice with methanol (80 mL)
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a7e22981418349d19aa8f4dd27058de7
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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