Sodium borohydride → (2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methanol

HRID 2267216Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=[O:12].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[OH:12]

Participants

Conditions

Temperature: 0 °C

Procedure

(2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methanone (1.0 g, 2.8 mmol) was dissolved in MeOH (15 mL) and cooled to 0° C. NaBH4 (318 mg, 8.4 mmol) was added. The reaction mixture was quenched by aq. NH4Cl (15 mL) and extracted with EtOAc (100, 30, and 20 mL). The combined extracts were washed with brine (15 mL), dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography (5:1, hexanes:EtOAc) to provide 3d (980 mg, 97%) as a white powder. 1H NMR (300 MHz, CDCl3): δ 7.69 (d, J=8.4 Hz, 1H), 7.38 (d, J=3.0 Hz, 1H), 7.31 (dd, J=8.2, 3.0 Hz, 1H), 6.91 (s, 2H), 6.61 (d, J=2.1 Hz, 1H), 3.85 (s, 3H); 13C NMR (75 MHz, CDCl3): δ 159.6, 137.8, 136.3, 133.9, 133.0, 130.5, 129.6, 129.6, 128.0, 126.6, 115.4, 115.4, 70.2, 55.9; IR (film): 3482 cm−1, 1438, 1410, 1325;

Workup

customThe reaction mixture was quenched by aq. NH4Cl (15 mL)
extractionextracted with EtOAc (100, 30, and 20 mL)
washThe combined extracts were washed with brine (15 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customPurification by silica gel chromatography (5:1, hexanes:EtOAc)

Sources & evidence

ORD record: ord-f8052c88e58f4ad699fa23c35250d7fb
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858825B2

Reaction notes

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