Bromide ion → HCID 21767387, compound

HRID 862585Notes

Reaction equation

HRID 862585 reaction equation
[Br-].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:12]1(C)C=CC=CC=1.[CH3:19][C:20]1[CH:21]=[C:22]([C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=1)[CH:23]=O.Cl>C1COCC1>[CH3:19][C:20]1[CH:21]=[C:22]([C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=1)[CH:23]=[CH2:12]

Participants

7

Reactant 5

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 1140TolueneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 118051105-Methyl-2-nitrobenzaldehyde

Product 1

HCID 21767387HCID 21767387, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a suspension of methyltriphenylphosphnium bromide (18.86 g, 52.8 mmol) in THF (120 mL) was added 0.5M potassium hexamethyldisilazide in toluene (106 mL, 53.0 mmol) at -10° C. The mixture was stirred for 40 min at the same temperature and 3-methyl-6-nitrobenzaldehyde (8.0 g, 48 mmol) in THF (60 mL) was added. The mixture was stirred for 1 h at -10° C. and 0.2N hydrochloric acid (400 mL) was added. The mixture was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 15:1 hexane/ethyl acetate to give 5.10 g of the title compound (65%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography with 15:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-865d8c6495ee4e14bdfd89edd6fa799f
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

Loading…