4'-(Trifluoromethyl)-4-biphenylcarbaldehyde → 3-Methyl-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-ol

HRID 1427463Notes

Reaction equation

HRID 1427463 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:19]([Mg]Br)[CH:20]([CH3:22])[CH3:21]>O1CCCC1>[CH3:19][CH:20]([CH3:22])[CH2:21][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)[OH:16]

Participants

4

Reactant 2

HCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehydeHCID 178418816HCID 178418816, compound

Product 1

HCID 597293893-Methyl-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-olYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 4′-(trifluoromethyl)biphenyl-4-carbaldehyde (7.0 g, 28 mmol) in tetrahydrofuran (280 mL) was added isobutylmagnesium bromide (21 mL, 2M in THF, 42 mmol) dropwise at −15° C. The reaction was stirred at −10° C. for 2 hours. The reaction was quenched with 1N HCl (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)butan-1-ol (3.9 g, 45%) as a solid. 1H NMR (400 MHz, CDCl3, δ): 7.62 (s, 4H), 7.52-7.50 (m, 2H), 7.40-7.38 (m, 2H), 4.77-4.73 (m, 1H), 1.75-1.67 (m, 1H), 1.50-1.46 (m, 2H), 0.92-0.90 (m, 6H).

Workup

  1. customThe reaction was quenched with 1N HCl (10 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-fa6b65d0774845688f3419165d3f8e08
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

Loading…