Ethanol → HCID 67102424, compound

HRID 2079856Notes

Reaction equation

HRID 2079856 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[C:10]1[CH:15]=[C:14](Br)[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:11]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:34]([C:37]1[CH:38]=[CH:39][C:40]([O:46][CH3:47])=[C:41](B(O)O)[CH:42]=1)([CH3:36])[CH3:35].C(O)C.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=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>[CH2:1]([O:8][C:9]([C:10]1[CH:15]=[C:14]([C:41]2[CH:42]=[C:37]([CH:34]([CH3:36])[CH3:35])[CH:38]=[CH:39][C:40]=2[O:46][CH3:47])[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:11]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 45891905-Isopropyl-2-methoxyphenylboronic acidHCID 46915635Benzyl-2,4-bis-benzyloxy-5-bromobenzoate

Product 1

HCID 67102424HCID 67102424, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2,4-bis-benzyloxy-5-bromo-benzoic acid benzyl ester (503 mg, 1 mmol) and 5-isopropyl-2-methoxy-phenylboronic acid (388 mg, 2 mmol) was heated in a mixture of toluene (5 ml), ethanol (5 ml) and saturated NaHCO3 (5 ml) under nitrogen in the presence of a catalytic amount of Pd(PPh3)4 (60 mg, 0.052 mmol) at 80° C. for 2-3 h. After the reaction was complete, the reaction mixture was extracted with ethyl acetate (25 ml×3), and the combined organics were washed with water and brine and dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to provide 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid benzyl ester (481 mg, 84%). M.p.: 139-141° C.; 400 MHz 1H NMR (CDCl3) δ: 7.44-7.22 (m, 16H), 7.17 (dd, J=8.0, 2.4 Hz, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.58 (s, 1H), 5.32 (s, 2H), 5.11 (s, 2H), 5.04 (s, 2H), 3.71 (s, 3H), 2.87 (hept, J=7.2 Hz, 1H), 1.23 (d, J=7.6 Hz, 6H); LCMS: 573 [M+H].

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (25 ml×3)
  2. washthe combined organics were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f34e2a1a672646fbb16f76d5798dc75a
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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