2,4,6-Trichlorobenzoic acid → tert-Butyl 3-bromobenzoate

HRID 1058579Notes

Reaction equation

HRID 1058579 reaction equation
Cl[C:2]1C=C(Cl)C=[C:7](Cl)[C:3]=1[C:4](O)=O.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18].C(N(CC)CC)C.C(O)(C)(C)C>C1COCC1.CN(C1C=CN=CC=1)C>[C:3]([O:18][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([Br:13])[CH:15]=1)([CH3:7])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 57642,4,6-Trichlorobenzoic acidHCID 6386tert-ButanolHCID 8471TriethylamineHCID 114563-Bromobenzoic acid

Product 1

HCID 334079tert-Butyl 3-bromobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,4,6-Trichlorobenzoic acid (11.7 ml, 75 mmol) was added dropwise to a solution of 3-bromobenzoic acid (15 g, 75 mmol), triethyl amine (10.5 ml, 75 mmol) in THF (25 ml) at RT. The reaction was stirred 15 min. Then, t-butanol (7.1 ml, 150 mmol) and DMAP (18.3 g, 150 mmol) were added and the reaction was stirred overnight. The crude reaction was filtered through a pad of silica gel, concentrated, and was used in the next reaction without further purification.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe crude reaction
  3. filtrationwas filtered through a pad of silica gel
  4. concentrationconcentrated
  5. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-11aa86becb8e46f385db819294b90b5c
Source dataset
uspto-grants-2003_02
Patent number
US06518267B1

Reaction notes

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