Pyridine → Tert-butyl 4-bromobenzoate

HRID 620096Notes

Reaction equation

HRID 620096 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 685154-Bromobenzoyl chloride

Product 1

HCID 11334366Tert-butyl 4-bromobenzoateYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 5.5 g of dry tert.-butanol and 7.08 g of dry pyridine is added a solution of 9.79 g of 4-bromobenzoyl chloride in 20 ml of anhydrous methylene chloride. The mixture is stirred under nitrogen for 2 days. The reaction mixture is then diluted with methylene chloride, and the organic solution extracted with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residual oil is distilled under reduced pressure to give 8.9 g (70%) of tert.-butyl 4-bromobenzoate as a colorless oil: b.p. 91°-92° C./1.2 mm; NMR (CDCl3, 80 MHz) delta 1.59 (s, 9H), 7.53 (d, 2H, J=8.7 Hz); IR (neat) 2970, 1710, 1585, 1475, 1390, 1290, 1160, 1110, 1070, 845 and 745 cm-1.

Workup

  1. extractionthe organic solution extracted with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. distillationThe residual oil is distilled under reduced pressure

Sources & evidence

ORD record
ord-5d702a61286142839c3e98d901d068b5
Source dataset
uspto-grants-1989_04
Patent number
US04818819

Reaction notes

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