Sodium borohydride → 2,3,5,6-Tetrafluoro-4'-hydroxymethyl-biphenyl-4-carboxylic acid methyl ester

HRID 1470662Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10]([F:11])=[C:9]([F:12])[C:8]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][CH:14]=2)=[C:7]([F:21])[C:6]=1[F:22])=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[C:6]([F:22])=[C:7]([F:21])[C:8]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=2)=[C:9]([F:12])[C:10]=1[F:11])=[O:4]

Participants

Conditions

Temperature: -10 °C

Procedure

2,3,5,6-Tetrafluoro-4′-formyl-biphenyl-4-carboxylic acid methyl ester (1.26 g, 4.03 mmol) was dissolved in methanol (30 mL) and cooled to −10° C. Sodium borohydride (0.76 g, 20.19 mmol) was added portion wise and reaction mixture stirred by maintaining the same temperature. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was concentrated to dryness. The obtained residue was redissolved in ethyl acetate (50 mL) and washed with water (20 mL×2) followed by brine, dried over anhydrous sodium sulphate and concentrated to get colorless solid (1.1 g, 86.75%).

Workup

customreaction mixture
temperatureby maintaining the same temperature
concentrationAfter completion, the reaction mixture was concentrated to dryness
dissolutionThe obtained residue was redissolved in ethyl acetate (50 mL)
washwashed with water (20 mL×2)
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-ca523cb9a0a64791bc519b4763ff9765
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006454B2

Reaction notes

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