Water → HCID 22619637, compound

HRID 840503Notes

Reaction equation

HRID 840503 reaction equation
B(Br)(Br)[Br:2].C[O:6][C:7]1[CH:27]=[CH:26][C:10]2[CH:11]([CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[CH2:14][CH2:15][C:9]=2[CH:8]=1.O>ClCCl>[BrH:2].[CH3:25][N:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH:11]1[C:10]2[CH:26]=[CH:27][C:7]([OH:6])=[CH:8][C:9]=2[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22619636HCID 22619636, compound

Product 1

HCID 22619637HCID 22619637, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
24.5 °C

Procedure

To 35 ml of freshly distilled dichloromethane was added 1.98 ml of boron tribromide. The reaction mixture was placed in a water bath. To the reaction mixture was added a solution of 1.1 g (3.5 mmol) of 5 in 15 ml of dichloromethane dropwise. The mixture was allowed to stir at room temperature (23-26° C.) for 30 minutes and poured into 50 g of ice/water. An additional 50 ml of water was added and extracted with 3×100 ml of chloroform. The combined organic layer was dried (Na2SO4) and concentrated to give 1.2 g (3.18 mmol, 90%) of 6 as an off-white solid.

Workup

  1. customThe reaction mixture was placed in a water bath
  2. extractionextracted with 3×100 ml of chloroform
  3. dry with materialThe combined organic layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b38abc8e7fa461dbd52e65886094663
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

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