1-Bromo-3-chloropropane → HCID 66869844, compound

HRID 57215

Reaction equation

HRID 57215 reaction equation
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Cl:24][CH2:25][CH2:26][CH2:27]Br.O.O.O.O.O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.CCOC(C)=O.[Cl-].[Na+].O.O.[I-].[Na+]>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:27][CH2:26][CH2:25][Cl:24])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

9

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 1151755-(Tetradecyloxy)-2-furoic acidHCID 86669148Tetrabutylammonium hydroxide pentahydrate

Product 1

HCID 66869844HCID 66869844, compoundYield 69.1%

Reagents, catalysts & solvents 5

HCID 5238Sodium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a vigorously stirred suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (0.650 g, 2.0 mmol) in 10 mL of N,N-dimethylformamide was added 3-chlorobromopropane (0.618 mL, 6.0 mmol), tetrabutylammonium hydroxide pentahydrate (0.734 g, 4.2 mmol) and sodium iodide (˜20 mg). The suspension appeared to go into solution briefly, and then a very finely dispersed white precipitate was observed. The reaction was allowed to stir for 12 hrs. The suspension was then diluted with EtOAc (100 mL), brine (50 mL) and water (50 mL). The phases were separated and the organic phase was washed with water (50 mL) and brine (50 mL). The organic phase was then dried and concentrated to yield 0.554 g of the title compound. This material was used in the subsequent step without further purification.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water (50 mL) and brine (50 mL)
  3. customThe organic phase was then dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d415c70e93b2457da7ef6543791e7477
Source dataset
uspto-grants-2016_09
Patent number
US09434718B2

Linked notes

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