Sodium Hydroxide → HCID 66784058, compound

HRID 1095825Notes

Reaction equation

HRID 1095825 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][C:12]3([CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[O:11][CH2:10][C:9]2=[O:27])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.ClCCl.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][C:12]3([CH2:14][CH2:15][N:16]([C:19]4[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=4)[CH2:17][CH2:18]3)[O:11][CH2:10][C:9]2=[O:27])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22277759Boron tribromide dichloromethaneHCID 66784260HCID 66784260, compound

Product 1

HCID 66784058HCID 66784058, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The methoxy compound (205 mg, 0.553 mmol) obtained in (a) was dissolved in chloroform, and at 0° C., 1.0 M boron tribromide/dichloromethane solution (2.2 ml, 2.2 mmol) was dropwise added thereto, and this was stirred overnight at room temperature. At 0° C., the reaction solution was neutralized by adding aqueous 2 N sodium hydroxide solution thereto, and extracted with chloroform, and the organic layer was washed with saturated saline. The organic layer was dried with sodium sulfate, and the solvent was evaporated off under reduced pressure to obtain the phenol compound as a crude product (165 mg, 84%).

Workup

  1. customAt 0° C.
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with saturated saline
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-35a298f2ff31483aa59474316d0afa35
Source dataset
uspto-grants-2012_03
Patent number
US08138206B2

Reaction notes

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