Water → 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

HRID 2382684Notes

Reaction equation

HRID 2382684 reaction equation
[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[NH:14]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2[CH:21]=[CH:22][CH:23]=[CH:24][C:15]1=2.C(N(CC)CC)C.O>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8]([N:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]2=3)(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

Product 1

HCID 684709361-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DCM (20 mL) containing 5-bromo-4-chloro-2-fluoro-benzenesulfonyl chloride (2.82 g, 9.2 mmol) was added 2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.35 g, 9.2 mmol) and triethylamine (2.8 mL, 21 mmol). The mixture was stirred for 16 hrs. The mixture was then diluted with 50 mL of DCM and repartioned with 50 mL of water. The organic layer was further washed with water (2×30 mL) and dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (9/1 to 6/1) yielded 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine as the pale yellow solid (2.70 g). NMR (CDCl3), δ, 8.059 (1H, d, J=7.2 Hz), 7.404 (1H, d, J=9.3 Hz), 7.202-7.218 (2H, q), 7.073-7.129 (1H, m), 7.860 (1H, d, J=7.8 Hz), 3.746 (2H, m), 2.750-2.813 (2H, m), 1.906-1.982 (2H, m), 1.639-1.678 (2H, m).

Workup

  1. washThe organic layer was further washed with water (2×30 mL)
  2. dry with materialdried over MgSO4
  3. concentrationConcentration and purification by silica gel column chromatography
  4. washeluting with hexane/ethyl acetate (9/1 to 6/1)

Sources & evidence

ORD record
ord-8ff2a23ae6cf4c3d9287cf8404824483
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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