1,2-Dichloroethane → Tert-butyl 3,5-dibromobenzoate

HRID 2212322Notes

Reaction equation

HRID 2212322 reaction equation
C(Cl)CCl.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Br:15])[CH:14]=1)[C:9]([OH:11])=[O:10].[C:16](O)([CH3:19])([CH3:18])[CH3:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl.N1C=CC=CC=1>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Br:15])[CH:14]=1)[C:9]([O:11][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:10]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 6386tert-ButanolHCID 12063Benzoic acid, 3,5-dibromo-

Product 1

HCID 21964570Tert-butyl 3,5-dibromobenzoateYield 63.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

EDC (14.0 g, 73.0 mmol) and DMAP (4.0 g) are added to a solution of 3,5-dibromobenzoic acid (10.0 g, 36.0 mmol) and tert-butanol (3.4 g, 46.8 mmol) in absolute CH2Cl2 (100 ml) and absolute pyridine (30 ml), and the mixture is stirred at RT for 1 h and then at 50° C. for 2 h. The reaction solution is diluted with CH2Cl2 (100 ml) and extracted with a semisaturated aqueous NH4Cl solution (200 ml) (2×), dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification by chromatography [toluene/acetone (95:5)] on a silica gel column gives the title compound (7.7 g) as slightly yellow crystals. TLC, silica gel, glass plates, [toluene/acetone (7.5:2.5)], Rf=0.78.

Workup

  1. waitat 50° C. for 2 h
  2. extractionextracted with a semisaturated aqueous NH4Cl solution (200 ml) (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered off
  5. concentrationconcentrated under reduced pressure
  6. customFurther purification by chromatography [toluene/acetone (95:5)] on a silica gel column

Sources & evidence

ORD record
ord-aa7618a5b433489682e9ff5a7b0c9159
Source dataset
uspto-grants-2006_09
Patent number
US07101911B2

Reaction notes

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