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Sodium Carbonate → HCID 69870925, compound

HRID 398176
Notes
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Reaction equation

HRID 398176 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1Br)([CH3:7])[CH3:6])[CH3:2].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:7])[CH3:6])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 69871067HCID 69871067, compound

Product 1

HCID 69870925HCID 69870925, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 702
Ethanol
Solvent
HCID 1140TolueneSolvent

Procedure

2-(4-Benzyloxy-2-bromo-phenoxy)-2-methyl-propionic acid ethyl ester (3.00 g, 7.63 mmol) and phenyl boronic acid (1.12 g, 9.15 mmol) were dissolved in toluene (75 mL)/ethanol (75 mL). The solution was degassed (2×), and tetrakis(triphenylphosphine)palladium (70 mg, 0.061 mmol) was added followed by aqueous 2M Na2CO3 solution (7.63 mL, 15.3 mmol). The reaction mixture was degassed (2×) and heated to reflux under argon for 16 h. The reaction mixture cooled and partitioned between ethyl acetate (200 mL) and H2O (75 mL). The organic layer was washed with brine (75 mL), dried (Na2SO4), and concentrated to a light brown oil (3.58 g). The crude product was used directly in the next reaction: 1H NMR (400 MHz, CDCl3) δ1.266 (t, 3H, J=7.1 Hz), 1.273 (s, 6H), 4.20 (q, 2H, J 7.1 Hz), 5.03 (s, 2H), 6.82 (dd, 1H, J=3.2, 9.0 Hz), 6.92 (d, 1H, J=8.8 Hz), 6.97 (d, 1H, J=3.0 Hz), 7.28-7.44 (m, 8H), 7.51-7.60 (m, 2H); MS (ES) m/e #[M+1].

Workup

  1. additionwas added
  2. customThe reaction mixture was degassed (2×)
  3. temperatureheated
  4. temperatureto reflux under argon for 16 h
  5. temperatureThe reaction mixture cooled
  6. custompartitioned between ethyl acetate (200 mL) and H2O (75 mL)
  7. washThe organic layer was washed with brine (75 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to a light brown oil (3.58 g)
  10. customThe crude product was used directly in the next reaction

Sources & evidence

ORD record
ord-03f5ad970a5a4d459206a6ee6aa5a560
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610696B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes