Sulfuric Acid → HCID 54414935, compound

HRID 2395596Notes

Reaction equation

HRID 2395596 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21](OC)=[O:22])[CH:15]=[C:16]([F:18])[CH:17]=1.OS(O)(=O)=O>C1(C)C=CC=CC=1.CCOCC>[Br:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH2:21][OH:22])[CH:15]=[C:16]([F:18])[CH:17]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 53839942HCID 53839942, compound

Product 1

HCID 54414935HCID 54414935, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

56 ml (0.056 mol) of a 1M solution of diisobutylaluminium hydride in toluene are added dropwise under a nitrogen atmosphere to a suspension of 7.2 g (0.0278 mol) of methyl 3-(3-bromo-5-fluorophenyl) -2-propenoate in 84 ml of anhydrous ether cooled to 0° C. The mixture is stirred for 30 min at 0° C. and then for 3 h at room temperature. The mixture is cooled in an ice bath and carefully hydrolyzed with 6N H2SO4. Separation is carried out by settling and the organic phase is washed with water, dried over Na2SO4, filtered and evaporated under vacuum. The residue is purified by chromatography on silica (eluent: 2/1 hexane/ethyl acetate). Yd.: 4.2 g (65%)

Workup

  1. waitfor 3 h at room temperature
  2. temperatureThe mixture is cooled in an ice bath
  3. customSeparation
  4. washthe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue is purified by chromatography on silica (eluent: 2/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ab0f8362116945818761204a75652ea7
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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