Hydrochloric Acid → HCID 15354720, compound

HRID 602500Notes

Reaction equation

HRID 602500 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[O:15]C)[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>ClCCCl.O>[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[OH:15])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 2829331Ethyl (2-methoxy-4-nitrophenyl)carbamate

Product 1

HCID 15354720HCID 15354720, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

(2-Methoxy-4-nitrophenyl)-carbamic acid ethyl ester (2.15 g) was dispensed in 1,2-dichloroethane (20 mL) and cooled to 0° C. Boron tribromide (2.0 mL) in 1,2-dichloroethane (10 mL) was added dropwise. The reaction mixture was stirred 10 minutes at 0° C. and 30 minutes at room temperature. The mixture was again cooled to 0° C., and water (10 mL) was added carefully. The reaction mixture was neutralised with saturated aqueous sodium bicarbonate and aqueous hydrochloric acid (5M). The resulting mixture was extracted with ethyl acetate (3×100 mL). The combined organic phase was washed with water (2×100 mL) and brine (100 mL), dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the title compound as brownish solid (1.96 g, 97%).

Workup

  1. temperatureThe mixture was again cooled to 0° C.
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×100 mL)
  3. washThe combined organic phase was washed with water (2×100 mL) and brine (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f7091dda24df4d39bdf4d1121abd558a
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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