Allyl bromide → HCID 118452603, compound

HRID 1773239Notes

Reaction equation

HRID 1773239 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1N.Br[CH2:13][CH:14]=[CH2:15].N(OC(C)(C)C)=O>CC#N>[CH2:15]([C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[F:1])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10906Tert-Butyl nitrite2×HCID 1012542-Fluoro-4-nitroaniline

Product 1

HCID 118452603HCID 118452603, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Fluoro-4-nitroaniline (5 g, 32.0 mmol) was added to a solution of 3-bromoprop-1-ene (41.5 mL, 480 mmol) and tert-butyl nitrite (5.76 mL, 48.0 mmol) in 32 mL of degassed anhydrous CH3CN at 18-19° C. under nitrogen. At the end of the addition of the arylamine, another half-equivalent of tert-butyl nitrite (1.180 mL, 16.01 mmol) was added; the reaction was stirred at room temperature for 1 hr. The reaction was concentrated under reduced pressure to remove the volatile material. The residue was purified by silica gel flash chromatography, 100% Heptane-5% Ethyl Acetate/95% Heptane, to give 1-allyl-2-fluoro-4-nitrobenzene (2.98 g). 1H NMR (400 MHz, DMSO-d6) δ 3.51 (dd, J=6.4, 1.1 Hz, 2H), 5.05-5.16 (m, 2H), 5.96 (ddt, J=16.8, 10.2, 6.6, 6.6 Hz, 1H), 7.56-7.62 (m, 1H), 8.03-8.11 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove the volatile material
  3. customThe residue was purified by silica gel flash chromatography, 100% Heptane-5% Ethyl Acetate/95% Heptane

Sources & evidence

ORD record
ord-bccbefc17e9c4bb39e37fb515acfe7e9
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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