Sodium Hydroxide → HCID 59557754, compound

HRID 2403720Notes

Reaction equation

HRID 2403720 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 6344DichloromethaneSolvent2×

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) CH2Cl2 (10 mL) was added dropwise. 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. custom0° C
  2. additionwas added
  3. customto quench
  4. customthe reaction
  5. customThe CH2Cl2 layer was separated
  6. washwashed with aqueous NaHSO3 and brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under reduced pressure
  9. customthe product was purified by column chromatography
  10. customto obtain pure intermediate AL (0.62 g)

Sources & evidence

ORD record
ord-ab345eeaf99c410697f63be67e99949c
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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