Hydrochloric Acid → HCID 11539495, compound

HRID 900489Notes

Reaction equation

HRID 900489 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:36])[CH:14]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1)[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1)=[O:17].C(=O)([O-])[O-].[Na+].[Na+].Cl>CO.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:11][O:12][C:13](=[O:36])[CH:14]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=1)[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:20][CH:19]=1)=[O:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 11690496HCID 11690496, compound

Product 1

HCID 11539495HCID 11539495, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-hydroxyphenylboronic acid (160 mg, 1.2 mmol) in MeOH (3 mL) was added to a stirred solution of methyl-4-(4-bromophenyl)-4-oxo-2-(3-trifluoromethyl-benzyl)butyrate (270 mg, 0.6 mmol) in toluene (10 mL). Tetrakis-(Triphenylphosphine)-palladium(0) (21 mg, 4 mol %) and 2 N sodium carbonate (0.75 mL, 1.5 mmol) were added and then the reaction was heated to 90° C. (oil bath temp.) for 4-5 h until complete (TLC control). The reaction mixture was cooled to room temperature, acidified to pH 3 with 0.5 N hydrochloric acid and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with water and sat'd aq NaCl, dried over anhyd MgSO4, filtered and concentrated. Trituration and filtration from MeOH afforded the title compound has a white solid (200 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe phases were separated
  4. extractionthe aqueous phase being further extracted with ethyl acetate (2×20 mL)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over anhyd MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationTrituration and filtration from MeOH

Sources & evidence

ORD record
ord-fb2d181e80a84db7b63e9c81f44dd4ea
Source dataset
uspto-grants-2008_04
Patent number
US07358364B2

Reaction notes

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