N-bromobutanimide → 5-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole

HRID 2420252Notes

Reaction equation

HRID 2420252 reaction equation
[F:1][C:2]1([F:12])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:4]=2[O:3]1.[Br:13]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[F:12][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][Br:13])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 138788692,2-Difluoro-5-methyl-2H-1,3-benzodioxole

Product 1

HCID 203113835-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxoleYield 96.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture of 2,2-difluoro-5-methyl-1,3-benzodioxole (29.0 g, 0.169 mole), N-bromosuccinimide (30.1 g, 0.169 mole), benzoyl peroxide (0.5 g) and carbon tetrachloride (50 ml) is refluxed for 2.5 hours. Carbon tetrachloride (50 ml) is then added to the hot reaction mixture and the solids are filtered off. The filtrate and washings are evaporated to yield 41.0 g of title product, a brown oil; nmr (CCl4) δ 4.38 (S, 2H), 6.8-7.4 (m, 3H). The product is used without further purification in the next step.

Workup

  1. temperatureis refluxed for 2.5 hours
  2. filtrationthe solids are filtered off
  3. customThe filtrate and washings are evaporated

Sources & evidence

ORD record
ord-75fbd8abd1d048eeb44d46e67c54cb7e
Source dataset
uspto-grants-1978_08
Patent number
US04110345

Reaction notes

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