Hydrogen Bromide → HCID 118647338, compound

HRID 530196Notes

Reaction equation

HRID 530196 reaction equation
[NH2:1][CH:2]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4].[BrH:12]>CCOCC.C(O)(=O)C>[BrH:12].[NH2:1][CH:2]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 3357701Methyl 2-amino-2-(furan-2-yl)acetate

Product 1

HCID 118647338HCID 118647338, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

The crude methyl 2-amino-2-(furan-2-yl)acetate (Example 2c) was dissolved in 350 mL of anhydrous ether and with rapid magnetic stirring, 10 mL of 33% wt HBr in acetic acid was added slowly by syringe. After stirring for 30 min, filtration followed by air drying gave methyl 2-amino-2-(furan-2-yl)acetate hydrobromide (12.35 g, 51.8 mmol, 54.2% yield) as an off-white solid; Mp 141-142° C. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (s, 2H), 7.81 (dd, J=1.8, 0.7 Hz, 1H), 5.68 (d. J=3.3 Hz, 1H), 6.56 (dd, =3.3, 1.9 Hz, 1H), 5.59 (s, 1H), 3.77 (s, 3H); 13C NMR (151 MHz, DMSO-d6) δ 167.44, 145.49, 145.06, 112.14, 111.70, 53.98, 49.73.

Workup

  1. additionwas added slowly by syringe
  2. filtrationfiltration
  3. customdrying

Sources & evidence

ORD record
ord-2058efb17f304aee966e2dafd4835e9a
Source dataset
uspto-grants-2016_05
Patent number
US09353060B2

Reaction notes

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