Methanol → HCID 86626343, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence