Hydrochloric Acid → tert-Butyl 2,4-dibromobutyrate

HRID 1604216Notes

Reaction equation

HRID 1604216 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 4h 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). 2M 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-b2e9f25520d34d7db5cb197609324293
Source dataset
uspto-grants-1999_11
Patent number
US05994312

Reaction notes

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