Sodium Carbonate → (3-Bromo-5-fluorophenyl)methanol

HRID 912043Notes

Reaction equation

HRID 912043 reaction equation
B.C1COCC1.[Br:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([F:17])[CH:16]=1)[C:11](O)=[O:12].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]([CH2:11][OH:12])[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 27733393-Bromo-5-fluorobenzoic acid

Product 1

HCID 2769402(3-Bromo-5-fluorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

BH3.THF in THF (1.00 M, 4.44 ml) was added dropwise into the THF (10 ml) solution of 3-bromo-5-fluorobenzoic acid (447 mg, 2.00 mmol) at rt under an atmosphere of nitrogen. The combined solution was stirred at rt for 24 h. After that time, the mixture was diluted with EtOAc (50 ml) and treated with saturated Na2CO3 (30 ml). The aqueous layer was extracted with EtOAc (2×25 ml). The extracts were washed with water (3×30 ml), brine (30 ml), dried over MgSO4, filtered and concentrated in vacuo to give the title compounds as colorless oil. 1H NMR (400 MHz, CDCl3): δ=1.83 (brs, 1H), 4.71 (s, 2H), 7.03-7.08 (m, 1H), 7.16-7.20 (m, 1H), 7.32-7.34 (m, 1H). HPLC: tR=2.87 min (polar—5 min, ZQ3).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (2×25 ml)
  2. washThe extracts were washed with water (3×30 ml), brine (30 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a599bde96ad5459d9af3fe1c52016c80
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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