5-Fluoro-2-nitrophenol → HCID 80207810, compound

HRID 1054163Notes

Reaction equation

HRID 1054163 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19]/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN1C(=O)CCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[O:11][CH2:19]/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 80207810HCID 80207810, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-fluoro-6-nitrophenol (200 g, 1.27 mol), anhydrous K2CO3 (202 g, 1.46 mol) and NMP (1.2 L) under nitrogen atmosphere was stirred at 25° C. for 30 min. Ethyl 4-bromocrotonate (80% tech., 252 mL, 1464 mmol) was added during 2-3 min to the obtained red suspension and the resulting mixture was stirred over night at ambient temperature. The yellowish suspension was then poured into ice-water (8.0 L) under stirring. After stirring for 1 h the solids were filtered off, washed with water (5×1.0 L), heptane (4×0.50 L) and then dried over night at 50° C. in vacuo affording the title compound (332 g, 1.20 mmol, 98% w/w, 95% yield).

Workup

  1. stirringthe resulting mixture was stirred over night at ambient temperature
  2. stirringunder stirring
  3. stirringAfter stirring for 1 h the solids
  4. filtrationwere filtered off
  5. washwashed with water (5×1.0 L), heptane (4×0.50 L)
  6. customdried over night at 50° C. in vacuo

Sources & evidence

ORD record
ord-6e9a1c57c5f34ed18612e00f031e2757
Source dataset
uspto-grants-2016_07
Patent number
US09394291B2

Reaction notes

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