Water → HCID 86625178, compound

HRID 1499319Notes

Reaction equation

HRID 1499319 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].C(N(CC)CC)C.[Br:16][C:17]([CH3:22])([CH3:21])[C:18](Br)=[O:19].[OH2:23]>ClCCl>[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[Br:16][C:17]([CH3:22])([CH3:21])[C:18]([O-:19])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 86625178HCID 86625178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Hydroxysuccinimide (11.51 g, 0.1 mol) was dissolved in anhydrous dichloromethane (100 ml) with triethylamine (28.1 mL, 0.2 mol) under nitrogen in a 250 ml round-bottomed flask equipped with a magnetic stirrer. The flask was cooled to 0° C. with an ice bath before the dropwise addition of 2-bromo-2-methylpropionyl bromide (13.9 mL, 0.11 mol). Next the mixture was stirred for 45 minutes and allowed to reach room temperature. After this the reaction mixture was poured into an excess of cold water and extracted with diethyl ether (3×50 mL). The organic layer was subsequently washed with a saturated aqueous solution of sodium carbonate (3×50 mL), acidified water (pH=4.5, 3×50 mLl), and again the saturated aqueous solution of sodium carbonate (3×50 mL). The organic layer was dried over anhydrous magnesium sulphate and filtered. Finally the solvent was removed under reduced pressure by using the rotary evaporator in order to isolate the title compound in quantitative yield as a white solid. 1H NMR (CDCl3) δ (ppm) 2.08 (s, 6H, C(CH3)2Br), 2.87 (s, 4H, Hcycl). 13C NMR (CDCl3) δ (ppm) 26.03 (2C, Ccycl), 31.09 (2C, C(CH3)2Br), 51.60 (1C, (CH3)2Br), 167.89 (1C, C═O), 169.02 (2C, Ccycl═O). IR (solid, ATR cell) ν (cm−1) 1803, 1772 (Ccycl═O), 1728 (C═O), 1394, 1359, 1197, 1121, 1071, 996, 924, 856, 811, 731, 648. Mass spectroscopy (+EI, m/z) 266, 265, 156, 151, 149, 123, 121, 116, 115, 91, 87, 70, 69. Elem. Anal. Theoretical for C8H10NO4Br: C, 36.39; H, 3.82; N, 5.30; Br, 30.26. Found: C, 36.35; H, 3.82; N, 5.03; Br, 30.17. Melting point 72-74° C.

Workup

  1. customequipped with a magnetic stirrer
  2. customto reach room temperature
  3. extractionextracted with diethyl ether (3×50 mL)
  4. washThe organic layer was subsequently washed with a saturated aqueous solution of sodium carbonate (3×50 mL)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customFinally the solvent was removed under reduced pressure
  8. customthe rotary evaporator in order

Sources & evidence

ORD record
ord-a8f35cdd200b4c8288a1e6470266f239
Source dataset
uspto-grants-2015_12
Patent number
US09200104B2

Reaction notes

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