Water → HCID 58979133, compound

HRID 1181145Notes

Reaction equation

HRID 1181145 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:23][O:24][C:25](=[O:32])[CH2:26][C:27](=[O:31])[CH:28](Br)[CH3:29].O>CC(C)=O>[CH3:23][O:24][C:25]([CH2:26][C:27](=[O:31])[CH:28]([O:8][C:7]([C:4]1[CH:3]=[CH:2][C:1]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)=[O:9])[CH3:29])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 58979133HCID 58979133, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of biphenyl-4-carboxylic acid (800 g, 4.03 mol) in acetone (4.6 L) was treated with triethylamine (0.6 L, 4.3 mol, 1.07 eq) dropwise over 13 min while maintaining the temperature at 15-30° C. 4-Bromo-3-oxo-pentanoic acid methyl ester (880 g, 4.21 mol, 1.04 eq) was added dropwise over 21 min at 15-30° C. The mixture was stirred overnight at room temperature. Water (9.6 L) was added dropwise over 85 minutes at 15-30° C. The mixture was stirred for 2 h. The precipitated product was collected by filtration and washed twice with water (1 L). The product was dried under vacuum at 50° C. to afford 1291 g (98% yield, 96% HPLC purity) of the title compound.

Workup

  1. stirringThe mixture was stirred for 2 h
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed twice with water (1 L)
  4. customThe product was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-117cd3ade43c4311ba0ca646f124a3f1
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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