Boron tribromide → HCID 135556678, compound

HRID 1072415Notes

Reaction equation

HRID 1072415 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([S:17][CH2:18][CH3:19])[N:14]3[CH:20]=[CH:21][N:22]=[C:13]3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[CH2:18]([S:17][C:15]1[N:14]2[CH:20]=[CH:21][N:22]=[C:13]2[CH:12]=[C:11]([C:5]2[CH:4]=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=2)[N:16]=1)[CH3:19]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11301507HCID 11301507, compound

Product 1

HCID 135556678HCID 135556678, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 7-(3,4-Dimethoxy-phenyl)-5-ethylsulfanyl-imidazo[1,2-c]pyrimidine (1.1 g, 3.5 mmol) in CH2Cl2 (25 ml) at 0° C., was added dropwise 1M solution of BBr3 in CH2Cl2 (25 ml, 25.0 mmol). The reaction mixture was stirred at 0° C. for 15 min and then at room temperature overnight. The mixture was then cooled using ice bath and ice-water was added, the precipitate was collected by filtration and then suspended in CH2Cl2 to give 4-(5-Ethylsulfanyl-imidazo[1,2-c]pyrimidin-7-yl)-benzene-1,2-diol. (875 mg, 87%)

Workup

  1. customat room temperature
  2. customovernight
  3. temperatureThe mixture was then cooled
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a6da5cfca8b94210a3989721fe5f1f65
Source dataset
uspto-grants-2005_06
Patent number
US06911443B2

Reaction notes

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