Boron tribromide → HCID 57835418, compound

HRID 730984Notes

Reaction equation

HRID 730984 reaction equation
[CH2:1]([C:3]([C:17]1[CH:30]=[CH:29][C:20]([O:21][CH2:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:19]([CH3:31])[CH:18]=1)([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([O:15]C)=[CH:14][C:8]=2[CH:7]=1)[CH2:4][CH3:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]([C:17]1[CH:30]=[CH:29][C:20]([O:21][CH2:22][C:23](=[O:28])[C:24]([CH3:25])([CH3:27])[CH3:26])=[C:19]([CH3:31])[CH:18]=1)([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:8]=2[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57835406HCID 57835406, compound

Product 1

HCID 57835418HCID 57835418, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{4-[1-ethyl-1-(5-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (0.86 g, 1.96 mmol) in CH2Cl2 (15.0 mL) at 0° C. is treated with BBr3 (3.0 mL, 2.94 mmol). The mixture is stirred for 2 h and quenched with water (10 mL). The aqueous layer is extracted with CH2Cl2 (30 mL). The organic layer is concentrated and purified using silica gel column chromatography (25% EtOAc/Hex) to afford the title compound (0.412 g, 50%).

Workup

  1. customquenched with water (10 mL)
  2. extractionThe aqueous layer is extracted with CH2Cl2 (30 mL)
  3. concentrationThe organic layer is concentrated
  4. custompurified

Sources & evidence

ORD record
ord-5131d457e16f4eb790ff157f3990f9b6
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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