Boron tribromide → HCID 11024320, compound

HRID 1359153Notes

Reaction equation

HRID 1359153 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:20]=[C:19]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([C:29](=[O:31])[CH3:30])=[CH:15][C:16]=3[C:17]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=3)=[CH:18]2)=[C:9]([CH3:32])[CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:20]=[C:19]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([C:29](=[O:31])[CH3:30])=[CH:15][C:16]=3[C:17]([C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)=[CH:18]2)=[C:9]([CH3:32])[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11143179HCID 11143179, compound

Product 1

HCID 11024320HCID 11024320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-28.5 °C

Procedure

BBr3 (100 ml, 1M in CH2Cl2) was added to the compound from Step A (6.76 g, 18.3 mmol) dissolved in CH2Cl2 (200 ml) at −60 to −70° C. The reaction was stirred overnight at −60 to 3° C. and then poured into water/ice (500 ml) and extracted with CHCl3/Acetone (2.5 L, 5/1). After evaporating the solvent, the residue was chromatographed on silica gel using a gradient of ethyl acetate:methanol (95:5) to ethyl acetate: methanol (80:20) to give the title compound. 1H-NMR (400 MHz, DMSO-d6) δH2.16 (3H, s, CH3), 2.67 (3H, s, COCH3), 6.52-8.48 (10H, ArH), 8.81 (1H, br, OH), 9.91 (1H, br, OH).

Workup

  1. extractionextracted with CHCl3/Acetone (2.5 L, 5/1)
  2. customAfter evaporating the solvent
  3. customthe residue was chromatographed on silica gel using a gradient of ethyl acetate:methanol (95:5) to ethyl acetate: methanol (80:20)

Sources & evidence

ORD record
ord-11956eab4fb14be88ff2c79598386ed7
Source dataset
uspto-grants-2003_07
Patent number
US06599921B2

Reaction notes

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