Carbon tetrabromide → HCID 67069911, compound

HRID 2390823Notes

Reaction equation

HRID 2390823 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=O.[BH4-].[Na+].C(Br)(Br)(Br)[Br:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CCO>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH2:7][Br:19])[CH:9]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 4311764Sodium borohydrideHCID 11747664HCID 11747664, compound

Product 1

HCID 67069911HCID 67069911, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromo-3-tert-butyl-2-methoxybenzaldehyde (0.30 g, 1.1 mmol; CASRN 417715-87-8) in EtOH (5 mL) at 0° C. was added NaBH4 (0.042 g, 1.1 mmol). The mixture was stirred for 1 h, and partitioned between 1N HCl and Et2O. The ether layer was evaporated, and the crude benzyl alcohol was dissolved in DCM and treated sequentially with CBr4 (0.55 g, 1.7 mmol) and PPh3 (0.45 g, 1.7 mmol). After stirring 2 h at RT, the reaction mixture was concentrated, and the crude product was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.34 g (90%) 5-bromo-1-bromomethyl-3-tert-butyl-2-methoxybenzene (114).

Workup

  1. custompartitioned between 1N HCl and Et2O
  2. customThe ether layer was evaporated
  3. dissolutionthe crude benzyl alcohol was dissolved in DCM
  4. stirringAfter stirring 2 h at RT
  5. concentrationthe reaction mixture was concentrated
  6. customthe crude product was purified by SiO2 chromatography
  7. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-dfe3a1f1e5c24ca3ad30fb29d80b05d3
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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