Sodium Carbonate → HCID 11266503, compound

HRID 2071131Notes

Reaction equation

HRID 2071131 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]=[C:12]([CH:18]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:8]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:18]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 1828531,3-Benzenedicarboxylic acid, 5-bromo-, diethyl ester

Product 1

HCID 11266503HCID 11266503, compound

Conditions

Temperature
35 °C

Procedure

A mixture of Na2CO3 (776 mg, 7.32 mmol), Pd (OAc)2 (4.5 mg, 0.02 mmol), diethyl 5-bromoisophthalate (1 g, 3.66 mmol), phenyl boronic acid (670 mg, 5.49 mmol), distilled water (14 mL) and acetone (12 mL) was stirred at 35° C. for 0.5 h. The reaction solution was then extracted four times with diethyl ether (4×20 mL). The combined organic phase washed with brine, dried over sodium sulfate and then filtered. The solvent was removed under vacuum, and the crude diethyl biphenyl-3,5-dicarboxylate was taken to the next step without any further purification.

Workup

  1. distillationdistilled water (14 mL) and acetone (12 mL)
  2. extractionThe reaction solution was then extracted four times with diethyl ether (4×20 mL)
  3. washThe combined organic phase washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum
  7. customthe crude diethyl biphenyl-3,5-dicarboxylate was taken to the next step without any further purification

Sources & evidence

ORD record
ord-bbd668d4637c434e866f20609a640190
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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