3-(4-Hydroxyphenyl)propionic acid → HCID 57526931, compound

HRID 1452672Notes

Reaction equation

HRID 1452672 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[F:13][C:14]1[CH:15]=[C:16](I)[CH:17]=[CH:18][C:19]=1[F:20].C(=O)([O-])[O-].[K+].[K+]>[Cu]Br.CN1CCCC1=O>[F:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[F:20])[O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 11430Potassium CarbonateHCID 27244441,2-Difluoro-4-iodobenzene

Product 1

HCID 57526931HCID 57526931, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 24593copper(I) bromideSolvent

Procedure

In a 50-mL RB-flask was added 3-(4-hydroxyphenyl)propionic acid (1.66 g, 10.0 mmol), 3,4-difluoroiodobenzene (2.40 g, 10.0 mmol), copper(I) bromide (0.100 g), potassium carbonate (2.76 g, 20.0 mmol), and n-methyl-2-pyrrolidone (20 mL) as solvent. The mixture was stirred for 5 min at room temperature and then heated to 140° C. (oil bath). After being stirred for 12 hours at 140° C., the reaction mixture was cooled to room temperature and diluted with EtOAC (100 mL). The diluted mixture was washed with citric acid (aq, 30 mL), water (3×50 mL, brine and dried over MgSO4. The removal of solvent in vacuo afforded crude which was purified by chromatography (0.901 g, 32%): 1H NMR (400 MHz, CDCl3) δ 11.44-11.06 (br, 1H), 7.24-7.14 (m, 2H), 7.14-7.00 (m, 1H), 7.00-6.86 (m, 2H), 6.86-6.75 (m, 1H), 6.75-6.61 (m, 1H), 2.94 (t, 2H, J=7.6 Hz), 2.68 (t, 2H, J=7.6 Hz); ESMS m/e: 277.2 (M−H+).

Workup

  1. temperatureheated to 140° C. (oil bath)
  2. stirringAfter being stirred for 12 hours at 140° C.
  3. temperaturethe reaction mixture was cooled to room temperature
  4. additiondiluted with EtOAC (100 mL)
  5. washThe diluted mixture was washed with citric acid (aq, 30 mL), water (3×50 mL, brine
  6. dry with materialdried over MgSO4
  7. customThe removal of solvent in vacuo
  8. customafforded crude which
  9. customwas purified by chromatography (0.901 g, 32%)

Sources & evidence

ORD record
ord-785eb78a12254824a7f73484a12e2855
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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