Methanol → HCID 86626343, compound

Temperature

-70 °C

To a solution of 2,2-difluoro-2-(4-methylsulfanylphenoxy)acetic acid ethyl ester (19.8 g, 75 mmol) in dry ether (200 ml) at −70° C., a 1 M solution of DIBALH in hexanes (113 ml, 113 mmol) was added slowly. Ater stirring for 2 h at −70° C., methanol (4 ml) and water (27 ml) were dropwise added and the reaction mixture was left stirring at rt for 30 min. The heterogeneous mixture was filtered through a plug of Celite and the filtrate was diluted with ether (200 ml). The organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated to yield 2,2-difluoro-2-(4-methylsulfanylphenoxy)-acetaldehyde monohydrate which was then converted to the title compound as described in Example 1, Steps 8-12 above. Note: In step 11, both the sulfur atoms were oxidized to sulfonyl group. 1HNMR (DMSO-d6): δ 9.05 (1H, s), 7.99 (2H, m), 7.52 (2H, dd), 7.41 (2H, d), 7.25 (2H, t), 4.39 (1H, q), 3.80 (1H, m), 3.51 (2H, m), 3.36 (3H, s), 3.35 (2H, m), 3.20 (1H, m), 1.39 (2H, m), 1.13 (1H, m), 1.02 (1H, m), 0.75 (1H, m), 0.59 (2H, m), 0.31 (2H, m). LC/MS: M+1: 600.2; M−1: 598.2.

1. waitthe reaction mixture was left
2. stirringstirring at rt for 30 min
3. filtrationThe heterogeneous mixture was filtered through a plug of Celite
4. additionthe filtrate was diluted with ether (200 ml)
5. washThe organic layer was washed with brine
6. dry with materialdried over sodium sulfate
7. customThe solvent was evaporated

ORD record

ord-6e2c50e117744e15b693fde30f2bbc75

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013186B2