1,2-Dibromobenzene → HCID 86601344, compound

HRID 1009250Notes

Reaction equation

HRID 1009250 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[Li]CCCC.[CH2:14]([C@H:18]1[CH2:22][O:21][CH:20]([C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[NH:19]1)[CH:15]([CH3:17])[CH3:16].[Cl-].[NH4+]>C1COCC1>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([C@H:20]([NH:19][C@@H:18]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:22][OH:21])[C:23]([F:28])([F:29])[C:24]([F:25])([F:27])[F:26])=[CH:7][CH:2]=1

Participants

6

Reactant 4

HCID 114141,2-DibromobenzeneHCID 25517Ammonium ChlorideHCID 11413942(4S)-4-isobutyl-2-(pentafluoroethyl)-1,3-oxazolidineHCID 178418339Butyllithium

Product 1

HCID 86601344HCID 86601344, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a −78° C. solution of dibromobenzene (9.85 g, 41.8 mmol) in 100 mL of THF was added nBuLi (16.5 mL of 2.5M hexanes solution, 41.2 mmol) giving a thick suspension. After stirring 10 min, a solution of (4S)-4-isobutyl-2-(pentafluoroethyl)-1,3-oxazolidine (3.3 g, 13 mmol) in 3 mL THF was added giving a dark brown solution. The solution was allowed to warm to room temperature, then was poured into saturated aqueous ammonium chloride and extracted with ether. Purification by silica gel chromatography (10% to 40% ethyl acetate/hexanes gradient) gave the title compound as a single diastereomer.

Workup

  1. customgiving a thick suspension
  2. customgiving a dark brown solution
  3. extractionextracted with ether
  4. customPurification by silica gel chromatography (10% to 40% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-c1362f42e43a4a45b150525a6417e6b9
Source dataset
uspto-grants-2011_07
Patent number
US07973037B2

Reaction notes

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