Potassium Bromide → 3-(3',5'-Difluorobiphenyl-4-yl)propanal

HRID 84050Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[CH:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH:17]=[O:18])=[CH:13][CH:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the compound obtained from step d above (0.7 g) in dichloromethane (10 mL), 2,2,6,6,-tetramethylpiperidine N-oxyl (4.36 mg) and potassium bromide (33.32 mg) were added at 0° C. under nitrogen atmosphere. Sodium hypochlorite (6.5 mL, 4% solution) was added at pH 8-9 (maintained by adding aqueous sodium bicarbonate solution). The reaction was stirred for 20 minutes at 0° C. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine. The organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to afford the title compound (0.57 g).

Workup

customThe organic layer was separated
extractionthe aqueous layer was extracted with dichloromethane
washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine
dry with materialThe organic layer was dried over anhydrous sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b764c0ac49c54c7991fc0f43d269c016
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846910B2

Reaction notes

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