Sodium Hydroxide → HCID 59557754, compound

HRID 425043Notes

Reaction equation

HRID 425043 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 59557735HCID 59557735, compound

Product 1

HCID 59557754HCID 59557754, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (4-(5-bromo-2-chlorobenzyl)phenyl)methanol (intermediate AK) (1 g) in CH2Cl2 (10 mL), the solution of Dess-Martin periodinane (DMP) (1.22 g) in CH2Cl2 (10 mL) was added dropwise at 0° C. The mixture was warmed to room temperature, and the reaction was monitored by TLC. After 1 h, CH2Cl2 was added to dilute the solution and 1 M NaOH was added to quench the reaction. The CH2Cl2 layer was separated and washed with aqueous NaHSO3 and brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the product was purified by column chromatography to obtain pure intermediate AL (0.62 g).

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. customThe CH2Cl2 layer was separated
  5. washwashed with aqueous NaHSO3 and brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated under reduced pressure
  8. customthe product was purified by column chromatography
  9. customto obtain pure intermediate AL (0.62 g)

Sources & evidence

ORD record
ord-6163956b4c224c2fbd01ed681a1f8c9f
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

Loading…