3-[4-(8,9-Dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acrylic Acid Methyl Ester → 3-[4-(6-Bromo-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acrylic Acid Methyl Ester

HRID 584573Notes

Reaction equation

HRID 584573 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][CH2:14][CH:13]=2)=[CH:8][CH:7]=1.C1C=C[NH+]=CC=1.[Br:30][Br-]Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][CH2:14][C:13]=2[Br:30])=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 693213003-[4-(8,9-Dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acrylic Acid Methyl Ester

Product 1

HCID 740638933-[4-(6-Bromo-8,9-dihydro-7H-benzocyclohepten-5-yl)-phenyl]-acrylic Acid Methyl EsterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the olefin (2b) (5.44 g, 17.9 mmol) in CH2Cl2 (300 mL) at 0° C. was added pyridinium bromide perbromide (90%, 7.0 g, 19.6 mmol) in portions over 0.5 h. After stirring 1 h the solution was washed with water, sat. NaHSO3, water and was dried (MgSO4). The solvent was removed under reduced pressure to give the bromide (2c) as an oil (6.85 g, 100%): 1H NMR (CDCl3) δ 7.69 (d, J=16.1 Hz, 1H), 7.50 (d, J=8.1 Hz, 2H), 7.20 (m, 5H), 6.80 (d, J=7.3 Hz, 1H), 6.43 (d, J=16.1 Hz, 1H), 3.81 (s, 3H), 2.79 (t, J=7.0 Hz, 2H), 2.60 (t, J=7.0 Hz, 2H), 2.30 (m, 2H); APcI m/z: 424 (M+H+CH3CN+, 100%).

Workup

  1. washwas washed with water, sat. NaHSO3, water
  2. dry with materialwas dried (MgSO4)
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bf23ea86d0994b09986de56d2702edcc
Source dataset
uspto-grants-2005_08
Patent number
US06927224B2

Reaction notes

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