Water → HCID 11481595, compound

HRID 920923Notes

Reaction equation

HRID 920923 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].CN([CH:19]=[O:20])C.O>C1COCC1>[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:9]2[C:8]=1[CH:19]([OH:20])[O:11][C:10]2=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 114563-Bromobenzoic acidHCID 178418339Butyllithium

Product 1

HCID 11481595HCID 11481595, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of n-butyllithium 1.6 M in hexanes (17.5 mL, 28.1 mmol) was added at −20° C. under argon 2,2,6,6-tetramethylpiperidine (4.7 mL, 28.1 mmol) in anhydrous THF (40 mL). After cooling (−50° C.), 3-bromobenzoic acid (2.54 g, 12.8 mmol) in anhydrous THF (10 mL) was added dropwise and the mixture was stirred for 1 h. The mixture was then treated with an excess of DMF (3.7 g, 50.4 mmol). The resulting solution was allowed to warm up to ambient temperature, after which water was added. The aqueous layer was washed with diethyl ether, and then acidified with 4M HCl. The mixture was diluted with diethyl ether and the organic layer was separated and dried with MgSO4. The residue was purified by crystallization using with EtOAc/PE to give the crude title product (1.18 g, yield: 41%).

Workup

  1. additionwas added dropwise
  2. washThe aqueous layer was washed with diethyl ether
  3. additionThe mixture was diluted with diethyl ether
  4. customthe organic layer was separated
  5. dry with materialdried with MgSO4
  6. customThe residue was purified by crystallization

Sources & evidence

ORD record
ord-7d32157d12714bfcbf0652144a59d829
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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