1-(Cyclopropanesulfonyl)-4-fluorobenzene → HCID 59559937, compound

HRID 1177248Notes

Reaction equation

HRID 1177248 reaction equation
COC(C1C=C(OC2C=CC(S(C)(=O)=O)=CC=2)C=C2OC(C)CC=12)=O.[C:26]([O:30][C:31]([C:33]1[CH:44]=[C:43]([OH:45])[C:36]2[CH2:37][C:38]([CH2:41][OH:42])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27].[CH:46]1([S:49]([C:52]2[CH:57]=[CH:56][C:55](F)=[CH:54][CH:53]=2)(=[O:51])=[O:50])[CH2:48][CH2:47]1>>[C:26]([O:30][C:31]([C:33]1[CH:44]=[C:43]([O:45][C:55]2[CH:56]=[CH:57][C:52]([S:49]([CH:46]3[CH2:48][CH2:47]3)(=[O:50])=[O:51])=[CH:53][CH:54]=2)[C:36]2[CH2:37][C:38]([CH2:41][OH:42])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32])([CH3:27])([CH3:28])[CH3:29]

Participants

4

Reactant 3

HCID 593468801-(Cyclopropanesulfonyl)-4-fluorobenzeneHCID 595599054-Hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl esterHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 59559937HCID 59559937, compound

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from 4-hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (227c) and 1-cyclopropanesulfonyl-4-fluoro-benzene. 1H NMR (400 MHz, CDCl3) δ 7.86 (d, J=8.59 Hz, 2 H) 7.23 (s, 1 H) 7.07 (d, J=8.59 Hz, 2 H) 3.73 (dd, J=11.87, 5.81 Hz, 1 H) 3.62 (d, J=7.58 Hz, 1 H) 3.16 (d, J=116.67 Hz, 1 H) 2.78 (d, J=16.67 Hz, 1 H) 2.48 (td, J=8.02, 4.67 Hz, 1 H) 1.55-1.58 (m, 12 H) 1.45 (s, 2 H) 1.36 (dd, J=4.67, 1.89 Hz, 2 H) 0.97-1.13 (m, 2 H); LCMS for C24H27O7S m/z 460.80 (M+H)+.

Sources & evidence

ORD record
ord-3d24dec7cbe24cfeb526b00416c13abe
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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