HCID 54572619, compound → 277331-50-7

HRID 1250116Notes

Reaction equation

HRID 1250116 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.O1CCCC1.[Pt](=O)=O>[C:1]([O:5][C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 54572619HCID 54572619, compound

Product 1

HCID 54177962277331-50-7Yield 58.6%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinum(IV) oxide (0.002 g, 0.032 mmol) was added to a solution of 3-(3-bromophenyl)acrylic acid tert-butyl ester (2.24 g, 7.90 mmol) in methanol (7 mL) and tetrahydrofuran (1 mL) at room temperature under a nitrogen atmosphere. The mixture was hydrogenated under a balloon pressure for 10 hours. The mixture was filtered and the filtrate was concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave 3-(3-bromophenyl)propionic acid tert-butyl ester as a clear oil (1.32 g, 58%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customPurification by flash chromatography
  4. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-9b6e73cb684c478d9fc7b31cd99612c0
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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