Sodium Carbonate → (4'-Fluorobiphenyl-2-yl)methanol

HRID 1877917Notes

Reaction equation

HRID 1877917 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][OH:15].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][OH:15])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 728502-Bromobenzyl alcoholHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 1392777(4'-Fluorobiphenyl-2-yl)methanol

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a mixture of 4-fluorophenylboronic acid (2.5 g, 13.4 mmol), 2-bromobenzyl alcohol (2.81 g, 20.1 mmol) and Pd(PPh3)4(0.25 g, 0.216 mmol) in DME (20 mL) is added an aqueous solution of Na2CO3 (11.5 mL, 2.7 M, 31 mmol). The mixture is heated to 115° C. in sealed vessel overnight. The reaction is allowed to cool to room temperature and is diluted with EtOAc and water. The aqueous layer is extracted further with EtOAc (2×). The combined organic layers are washed with water, saturated NH4Cl, brine and dried over Na2SO4. After concentration, the resulting residue is purified by flash chromatography (hexane/CH2Cl2) to give (4′-fluorobiphenyl-2-yl)-methanol as oil. (cas # 773871-75-3) 1H NMR (400 MHz, CDCl3) δ (ppm) 7.46-7.43 (m, 1H), 7.32-7.22 (m, 4H), 7.18-7.16 (m, 1H), 7.04-6.99 (m, 2H), 4.48 (d, J=5.5 Hz, 2H), 1.68 (br s, 1H).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous layer is extracted further with EtOAc (2×)
  3. washThe combined organic layers are washed with water, saturated NH4Cl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe resulting residue is purified by flash chromatography (hexane/CH2Cl2)

Sources & evidence

ORD record
ord-fef1d00a258647f08dc1119eb1cfa878
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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