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 2253437Notes

Reaction equation

HRID 2253437 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-ab145cac7d1f44e6b3c2025e20fc2c72
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Reaction notes

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