Azobisisobutyronitrile → 1-(Bromomethyl)-3-(3-fluorophenoxy)benzene

HRID 1733486Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][Br:16]

Participants

Conditions

Temperature: 10 °C

Procedure

90 g (0.445 mol) of 3-(3-fluorophenoxy)-toluene were dissolved in 300 ml of anhydrous carbon tetrachloride and heated under reflux together with 79.3 g of N-bromosuccinimide. After reaching 70° C., 5 g of azodiisobutyronitrile were added. After about 10-20 minutes the reaction commenced, with evolution of heat, and after the exothermic reaction had subsided the mixture was heated for a further 4 hours under reflux. The reaction batch was then cooled to 10° C., the succinimide was filtered off and the carbon tetrachloride was distilled of in vacuo. The oil which remained was distilled at 143°-150° C./1 mm Hg. 72.9 g (58.2% of theory) of 3-(3-fluorophenoxy)-benzyl bromide were obtained.

Workup

temperatureheated
customAfter reaching 70° C.
customAfter about 10-20 minutes the reaction commenced
temperaturewith evolution of heat
customafter the exothermic reaction
temperaturewas heated for a further 4 hours
temperatureunder reflux
filtrationthe succinimide was filtered off
distillationthe carbon tetrachloride was distilled of in vacuo
distillationThe oil which remained was distilled at 143°-150° C./1 mm Hg

Sources & evidence

ORD record: ord-102c4e2d891548d3b2f4398ba999d1a3
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04242357

Reaction notes

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