Sulfuric Acid → HCID 52448820, compound

HRID 2362375Notes

Reaction equation

HRID 2362375 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:13][CH:14](O)[CH3:15].OS(O)(=O)=O.[OH-].[Na+].CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1>C(OC(=O)C)C>[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([O:12][CH:14]([CH3:15])[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 776461m-Bromocinnamic acid

Product 1

HCID 52448820HCID 52448820, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-(3-bromophenyl)acrylic acid (7.5 g, 32.4 mmol) in propan-2-ol (50 mL, 832 mmol) was added dropwise H2SO4 (0.431 mL, 8.09 mmol). The reaction was heated to reflux for 18 h then it was concentrated in vacuo providing a brown liquid which was redissolved in 50 mL ethylacetate. 1N NaOH was added dropwise until the aqueous mixture reached pH10. The organic layer was collected and washed with aqueous sodium bicarbonate (sat), brine, dried over magnesium sulfate, filtered and concentrated providing (E)-isopropyl 3-(3-bromophenyl)acrylate (8.4202 g, 29.7 mmol, 92% yield) as a yellow liquid. 1H NMR (500 MHz, DMSO) δ 7.98 (s, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.67-7.55 (m, 2H), 7.37 (t, J=7.9 Hz, 1H), 6.70 (d, J=16.0 Hz, 1H), 5.02 (dt, J=12.5, 6.2 Hz, 1H), 1.26 (d, J=6.3 Hz, 6H). Mass spec.: 270.88 (MH)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 18 h
  3. concentrationit was concentrated in vacuo
  4. customproviding a brown liquid which
  5. customThe organic layer was collected
  6. washwashed with aqueous sodium bicarbonate (sat), brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c8e56dcbb6b04514aca8914c40a14240
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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