Bromine → 7-bromo-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine

HRID 37423Notes

Reaction equation

HRID 37423 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1.[Br:14]Br>C(Cl)Cl>[Br:14][C:10]1[CH:11]=[CH:12][C:5]2[O:4][CH2:3][C:2]([CH3:13])([CH3:1])[CH2:8][O:7][C:6]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 19935415HCID 19935415, compound

Product 1

HCID 199355317-bromo-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepineYield 108.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8.55 g of 3,4-dihydro-3,3-dimethyl-2H-1,5-benzodioxepine (see Example 10) were dissolved in 70 ml of methylene chloride (CH2Cl2) and treated at 0° C. under an Argon atmosphere with a solution of 8.0 g of Br2 in 30 ml of CH2Cl2. The mixture was warmed to room temperature and left to react for 1 hour. It was then poured on to ice and extracted with ether. Washing with NaHCO3 solution and water, drying and evaporation yielded 13.35 g of 7-bromo-3,4-dihydro-3,3-dimethyl-2H-1,5-benzodioxepine as a colorless oil which was 94.5% pure and which contained 4.7% of starting material; it was processed in the crude state.

Workup

  1. waitleft
  2. customto react for 1 hour
  3. additionIt was then poured on to ice
  4. extractionextracted with ether
  5. washWashing with NaHCO3 solution and water
  6. customdrying
  7. customevaporation

Sources & evidence

ORD record
ord-86e367df791e43c89c0c9f5ccfdbced5
Source dataset
uspto-grants-1995_05
Patent number
US05420273

Reaction notes

Loading…