Water → HCID 22168653, compound

HRID 2260772Notes

Reaction equation

HRID 2260772 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22].O>CN(C=O)C>[NH2:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([O:6][CH2:22][CH:21]=[CH2:20])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 22168653HCID 22168653, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-5-nitrobenzoic acid (4.16 g, 22.5 mM) was dissolved in DMF (45 ml), and anhydrous K2CO3 (4.65 g, 33.7 mM) added with stirring. Allyl bromide (2.38 ml, 28.1 mM) was run in, the mixture was stirred for 18 hours at ambient temperature before being poured into water (450 ml) and extracted with diethyl ether (3×100 ml). The combined extracts were dried over MgSO4, and evaporated to give a yellow oil (5.4 g). The oil was purified by chromatography on silica, eluting with a mixture of ethyl acetate/hexane (12.5:87.5), to give allyl 2-fluoro-5-nitrobenzoate (4.64 g, 92%). Nmr (CDCl3): δ4.89 (d, 2H); 5.30-5.50 (m, 2H); 5.90-6.10 (m, 1H); 7.32 (t, 1H); 8.38-8.46 (m, 1H); 8.86 (dd, 1H).

Workup

  1. stirringwas stirred for 18 hours at ambient temperature
  2. extractionextracted with diethyl ether (3×100 ml)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-78668c5cf9194f0d9cb107a9043edc83
Source dataset
uspto-grants-1995_12
Patent number
US05478820

Reaction notes

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