Boron tribromide → HCID 135947948, compound

HRID 852906Notes

Reaction equation

HRID 852906 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 111487392-chloro-4-(4-methoxyphenyl)pyrimidine

Product 1

HCID 135947948HCID 135947948, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17 (3.7 g, 16.8 mmol) in dry dichloromethane (42 mL) at 0° C. was added boron tribromide (3.17 mL, 33.5 mmol). The mixture was stirred vigorously at room temperature for 16 h, cooled down to 0° C. Ice-water was poured-in and the stirring was continued for 30 min. The reaction mixture was concentrated to form a precipitate which was collected by filtration, washed with water, dried and purified by flash chromatography on silica gel (MeOH/CH2Cl2: 2/98) to afford the title compound 18 (3.28 g, 15.9 mmol, 94% yield). 1H NMR: (400 MHz, DMSO-d6) δ (ppm): 10.26 (s, 1H), 8.66 (d, J=5.6 Hz, 1H), 8.05 (td, J=8.4, 1.6 Hz, 2H), 7.96 (d, J=5.6 Hz, 1H), 6.90 (td, J=8.4, 1.6 Hz, 2H).

Workup

  1. temperaturecooled down to 0° C
  2. waitwas continued for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. customto form a precipitate which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried
  8. custompurified by flash chromatography on silica gel (MeOH/CH2Cl2: 2/98)

Sources & evidence

ORD record
ord-4fc28c25f07c4d91b0e0ea95b2926e3b
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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