Hydrochloric Acid → tert-Butyl 2,4-dibromobutyrate

HRID 567685Notes

Reaction equation

HRID 567685 reaction equation
[Br:1]Br.[Br:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].C(N(CC)CC)C.Cl.[C:18]([OH:22])([CH3:21])([CH3:20])[CH3:19]>ClCCl>[Br:1][CH:6]([CH2:5][CH2:4][Br:3])[C:7]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 8471TriethylamineHCID 24408BromineHCID 702254-Bromobutyryl chloride

Product 1

HCID 5107723tert-Butyl 2,4-dibromobutyrateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (31.3 ml, 0.54 mol) was added dropwise over 4 h at 100° C. to neat stirring 4-bromobutyryl chloride (100 g, 0.54 mol). The resulting acid chloride was cooled then added dropwise at 0° C. to a stirred solution of tert-butanol (240 ml) and triethylamine (64 ml, 0,461 mol) in anhydrous dichloromethane (600 ml). 2 M Hydrochloric acid was added and the layers separated. The organic portion was then washed sequentially with 10% sodium metabisulphite solution (2×500 ml), water (500 ml) and brine (500 ml), dried (MgSO4) and evaporated in vacuo to provide the title compound (120 g, 86%) as a brown liquid.

Workup

  1. customthe layers separated
  2. washThe organic portion was then washed sequentially with 10% sodium metabisulphite solution (2×500 ml), water (500 ml) and brine (500 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-186465854c50461294eda7223ad53620
Source dataset
uspto-grants-2001_01
Patent number
US06180611B2

Reaction notes

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