Sodium Carbonate → HCID 17952741, compound

HRID 1394574Notes

Reaction equation

HRID 1394574 reaction equation
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[CH3:11][O:12][CH2:13][O:14][C:15]1[C:20]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][C:18]([CH2:25][CH3:26])=[CH:17][C:16]=1B(O)O.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>[OH:10][C:5]1[CH:4]=[CH:3][C:2]([C:16]2[CH:17]=[C:18]([CH2:25][CH3:26])[CH:19]=[C:20]([C:21]([CH3:24])([CH3:22])[CH3:23])[C:15]=2[O:14][CH2:13][O:12][CH3:11])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 728635-BromosalicylaldehydeHCID 17952774HCID 17952774, compound

Product 1

HCID 17952741HCID 17952741, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 91 mg (0.078 mmol, 5%) of Pd(PPh3)4 and 252 mg (1.26 mmol) of 5-bromo salicylaldehyde in 10 mL of dry toluene was added 685 mmol (2.5 mmol, 2 equivalents) of 2-methoxymethoxy-3-tert-butyl-5-ethyl phenylboronic acid diluted in 5 mL of ethanol followed by 1.3 mL of a 2N aqueous solution of Na2CO3. The mixture was stirred at reflux for 3 hours and after cooling extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated under reduced pressure. The residual oil was purified over silica gel (eluent: ethyl acetate/hexane: 10/90) to give 333 mg (0.969 mmol, yield: 77%) of 2-hydroxy-5-(5-ethyl-3-tert-butyl-2-methoxymethoxyphenyl)-benzaldehyde a pale brownb oil. 1H NMR (CDCl3), δ: 11.04 (s, 1H), 9.95 (s, 1H), 7.75 (dd, J=8.9, 2.1 Hz, 1H), 7.74 (d, J=2.1 Hz, 1H), 7.19 (d, J=2.1 Hz, 1H), 7.06 (d, J=8.9 Hz, 1H), 6.98 (d, J=1.9 Hz, 1H), 4.52 (s, 2H), 3.29 (s, 3H), 2.64 (dd, J=15.2, 7.6 Hz, 2H), 1.47 (s, 9H), 1.26 (t, J=7.4 Hz, 3H).

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureafter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residual oil was purified over silica gel (eluent: ethyl acetate/hexane: 10/90)

Sources & evidence

ORD record
ord-cef16ed452e74ea8a3e2d89d0379ac41
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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