Water → 10a-(4-Chloro-benzenesulfonyl)-1,4,7-trifluoro-6a, 9,10,10a-tetrahydro-6H, 7H-benzo[c]chromen-8-one

HRID 1047503Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C@@:11]23[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][C@H:12]2[CH2:13][O:14][C:15]2[C:20]3=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B-](F)(F)(F)[F:29].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]23[CH2:26][CH2:25][C:24](=[O:27])[CH:23]([F:29])[CH:12]2[CH2:13][O:14][C:15]2[C:20]3=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of trans-10a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6a,9,10,10a-tetrahydro-6H,7H-benzo[c]chromen-8-one in DMF (4 mL) was added Selectfluor®. The reaction mixture was heated at 50° C. overnight, cooled to rt and water was added to precipitate the desired product. The product was isolated by filtration washing with water then dried under vacuum to provide a colorless solid. 1H NMR CDCl3 400 MHz) δ 7.61 (d, 2H), 7.53 (d, 2H), 7.19-7.14 (m, 1H), 6.55-6.49 (m, 1H), 5.20 (d, 1H), 4.74 (dd, 2JH-F=46.7 Hz, 3JH-F=11.8 Hz, 1H) 4.66 (d, 1H), 3.18 (t, 1H), 2.9 (m, 1H), 2.53 (m, 1H), 2.41 (m, 1H), 2.18 (m, 1H); LCMS (MH+) 431.

Workup

temperaturecooled to rt
customto precipitate the desired product
customThe product was isolated by filtration
washwashing with water
customthen dried under vacuum
customto provide a colorless solid

Sources & evidence

ORD record: ord-bc897b270af34ed2ad5c0c2f0f94f68c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569521B2

Reaction notes

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