Boron tribromide → 2-Hydroxy-6-methyl-4-phenoxy-benzaldehyde

HRID 1798144Notes

Reaction equation

HRID 1798144 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[C:7]([CH3:18])[C:4]=1[CH:5]=[O:6].B(Br)(Br)Br.C(=O)=O.CC(C)=O>C(Cl)Cl>[OH:2][C:3]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]=[C:7]([CH3:18])[C:4]=1[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 18522661Acetone cardiceHCID 582925842-Methoxy-6-methyl-4-phenoxy-benzaldehyde

Product 1

HCID 582926472-Hydroxy-6-methyl-4-phenoxy-benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A light yellow solution of 2-methoxy-6-methyl-4-phenoxy-benzaldehyde (6.33 g, 26.13 mmol) in DCM (250 mL) was treated with boron tribromide (1.0 M solution in DCM, 76 mL, 76 mmol) dropwise at −78° C. (dry ice/acetone bath). The red/brown mixture was stirred at −78° C. for 30 minutes, 0° C. (ice-water bath) for 30 minutes, then rt for 3 h. The mixture was quenched with ice water, then extracted with EtOAc. The extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to a brown residue. The residue was purified by column chromatography (SiO2, EtOAc/hexanes; 1:9) to afford 2-hydroxy-6-methyl-4-phenoxy-benzaldehyde (5.06 g, 85%), as a white solid. 1H NMR (400 MHz, CDCl3) δ 12.32 (s, 1H), 10.14 (s, 1H), 7.42 (t, J=7.42 Hz, 2H), 7.30-7.21 (m, 1H), 7.08 (d, J=7.42 Hz, 2H), 6.35 (s, 1H), 6.21 (s, 1H), 2.54 (s, 3H).

Workup

  1. customThe mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a brown residue
  7. customThe residue was purified by column chromatography (SiO2, EtOAc/hexanes; 1:9)

Sources & evidence

ORD record
ord-c92cca71a3fb4d5da99a508fd06853a8
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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