Bromine → HCID 57504581, compound

HRID 1098094Notes

Reaction equation

HRID 1098094 reaction equation
[Br:1]Br.[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH:10]([C:14]([OH:16])=[O:15])[C:11]([OH:13])=[O:12].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>Br.C(OCC)C>[Br:1][C:10]([CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH3:3])([C:14]([OH:16])=[O:15])[C:11]([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 24408Bromine2×HCID 656671Sodium PyrosulfiteHCID 20728366Poly(oxy-1,2-ethanediyl), α-(3,3-dicarboxypropyl)-ω-methoxy-

Product 1

HCID 57504581HCID 57504581, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

HBr (4.1 M in acetic acid, two drops) and bromine (1.44 g, 9.01 mmol) was added to a stirred solution of [2-(2-methoxyethoxy)ethyl]malonic acid (Step 2) (1.75 g, 8.49 mmol) in diethyl ether. The reaction mixture was kept at ambient temperature for 20 minutes when most of the bromine colour had disappeared. Sodium pyrosulfite (5% in water) was added and the two phases were separated. The aqueous phase was extracted with diethyl ether two times. The organic extracts were combined and washed with water. The organic phase was dried over MgSO4 and concentrated in vacuo to give the title product as a colourless solid (1.91 g), 1H NMR (300 MHz, CDCl3) δ 6.91 (br s, 2H), 3.75 (t, 2H), 3.62 (m, 4H), 3.42 (s, 3H), 2.70 (t, 2H).

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous phase was extracted with diethyl ether two times
  3. washwashed with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0132262af794e61bd78f60ecb515ffd
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…