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

HRID 2419348Notes

Reaction equation

HRID 2419348 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 product as a brown oil; nmr (CCl4) δ 4.38 (S, 2H), 6.8-7.4 (m, 3H). The product is used without 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-2b91703464e34a3aa3aaa7cb8ee458d3
Source dataset
uspto-grants-1978_08
Patent number
US04105780

Reaction notes

Loading…