Ethyl Acetate → 4-Bromo-2-chlorobenzaldehyde

HRID 40278

Reaction equation

HRID 40278 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([Cl:10])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 141091094-Bromo-2-chlorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (4-bromo-2-chlorophenyl)methanol (4.5 g, 20 mmol) in DCM (50 mL) was added Dess-Martin periodinane (9.3 g) at 23° C. Reaction refluxed after addition. After 20 min, TLC (1:4 EtOAc/Hex) suggests full conversion of alcohol. Suspension then washed with 5% NaHCO3 (100 mL plus 15 g dry NaHCO3). Organic dried over MgSO4, concentrated onto dry silica (15 g), then purified on silica (120 g) eluting with 0>10% EtOAc/hex. 4-bromo-2-chlorobenzaldehyde isolated as a white solid.

Workup

  1. customReaction
  2. temperaturerefluxed
  3. additionafter addition
  4. washSuspension then washed with 5% NaHCO3 (100 mL plus 15 g dry NaHCO3)
  5. dry with materialOrganic dried over MgSO4
  6. concentrationconcentrated onto dry silica (15 g)
  7. custompurified on silica (120 g)
  8. washeluting with 0>10% EtOAc/hex

Sources & evidence

ORD record
ord-984b65d988c24067b307706642a1f037
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Linked notes

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