Bromine → 2-bromo-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one

HRID 1036374Notes

Reaction equation

HRID 1036374 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[Br:12]Br>C(O)(=O)C>[Br:12][C:5]1[S:1][C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 123415575,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one

Product 1

HCID 685259082-bromo-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a solution of 5,6,7,8-tetrahydro-cyclohepta[b]thiophen-4-one (0.5 g, 3 mmol) in 50% aqueous acetic acid (5 mL), cooled to −5° C., was added dropwise a solution of bromine (0.15 mL) in acetic acid (3 mL). The reaction mixture was stirred at −5° C. for 1 hour and quenched into aqueous sodium acetate. The resulting precipitate was filtered off to give the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 7.36 (s, 1 H), 3.01 (m, 2 H), 2.71 (m, 2H), 1.94 (m, 4 H); MS (DCI/NH3) m/z 245 (M+H)+.

Workup

  1. customquenched into aqueous sodium acetate
  2. filtrationThe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-b09a324e136d4a23b0f17d1b52a55dfb
Source dataset
uspto-grants-2013_10
Patent number
US08546410B2

Reaction notes

Loading…