Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate → 4-(4-tert-Butoxycarbonyl-3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1643588Notes

Reaction equation

HRID 1643588 reaction equation
COC(C1C=C(OC2C=CC(C(N3CCC3)=O)=CC=2)C2CC(C)(C)OC=2C=1)=O.[CH3:29][O:30][C:31]([C:33]1[CH:43]=[C:42]([OH:44])[C:36]2[CH2:37][C:38]([CH3:41])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32].[C:45]([O:49][C:50](=[O:60])[C:51]1[C:56]([F:57])=[CH:55][C:54](Br)=[CH:53][C:52]=1[F:59])([CH3:48])([CH3:47])[CH3:46]>>[CH3:29][O:30][C:31]([C:33]1[CH:43]=[C:42]([O:44][C:54]2[CH:53]=[C:52]([F:59])[C:51]([C:50]([O:49][C:45]([CH3:47])([CH3:46])[CH3:48])=[O:60])=[C:56]([F:57])[CH:55]=2)[C:36]2[CH2:37][C:38]([CH3:41])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32]

Participants

4

Reactant 3

HCID 25067323Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateHCID 53432588Tert-butyl 4-bromo-2,6-difluorobenzoateHCID 595602514-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 595604264-(4-tert-Butoxycarbonyl-3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 35b, from 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) and 4-bromo-2,6-difluoro-benzoic acid tert-butyl ester. 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1 H) 7.23 (s, 1 H) 6.48 (d, J=8.84 Hz, 2 H) 3.89 (s, 3 H) 2.88 (s, 2 H) 1.59 (s, 9 H) 1.49 (s, 6 H); LCMS for C23H24F2O6 m/z 457.20 (M+Na)+.

Sources & evidence

ORD record
ord-36ffd55acbd342d9b858016424246dec
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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