Sodium Carbonate → HCID 67487863, compound

HRID 1880574Notes

Reaction equation

HRID 1880574 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8](=[CH2:12])[CH2:9][CH2:10][OH:11].[Cl:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1>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.COCCOC>[Cl:13][C:14]1[CH:19]=[C:18]([C:8](=[CH2:12])[CH2:9][CH2:10][OH:11])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5339753-Bromo-3-buten-1-olHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 67487863HCID 67487863, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of DME (20 mL) and 2M Na2CO3 (15 mL) containing 3-bromobut-3-en-1-ol (1.40 g, 7.66 mol), (3-chlorophenyl)boronic acid (2.3 g, 14.7 mmol) and Pd(PPh3)4 (0.4 g, 0.35 mmol) was refluxed under an argon atmosphere for 3 hours. The solution was concentrated (to remove excess DME) and partitioned between water and ethyl acetate. The organic phase was washed with 1N NaOH, water (2×) and brine. The solution was then dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.42 (s, 1H); 7.31-7.29 (m, 3H); 5.43 (s, 1H); 5.21 (s, 1H); 3.73 (t, J=6.5 Hz, 2H); 2.77 (t, J=6.3 Hz, 2H); 1.91 (s, 1H). LCMS1 2.95 min. (M-OH)=165.

Workup

  1. temperaturewas refluxed under an argon atmosphere for 3 hours
  2. concentrationThe solution was concentrated
  3. custom(to remove excess DME)
  4. custompartitioned between water and ethyl acetate
  5. washThe organic phase was washed with 1N NaOH, water (2×) and brine
  6. dry with materialThe solution was then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-740fef80c0a74620b6bc919dc05b8eb6
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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