Benzyl Alcohol → HCID 59394770, compound

HRID 453125Notes

Reaction equation

HRID 453125 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[C:17]=1[F:26]>CCOC(C)=O>[CH2:7]([O:14][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[C:17]=1[F:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 11430Potassium CarbonateHCID 469413031,2-Difluoro-3-methyl-4-nitrobenzene

Product 1

HCID 59394770HCID 59394770, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To a suspension of potassium carbonate (19.2 g, 138 mmol) and benzyl alcohol (22 mL) is added 1,2-difluoro-3-methyl-4-nitrobenzene (12 g, 69 mmol, ref. WO2007121416) and the mixture is heated to 180° C. for 2 h. The reaction mixture is then diluted with EtOAc and washed with water. The organic layer is concentrated and the residue is separated with FCC (EtOAc/heptane from 0 to 20%) to give 1-benzyloxy-2-fluoro-3-methyl-4-nitrobenzene. 1H NMR (400 MHz, MeOD) δ ppm 7.87 (dd, J=9.35, 2.02 Hz, 1 H), 7.44-7.47 (m, 2 H), 7.32-7.41 (m, 3 H), 7.17 (t, J=8.72 Hz, 1 H), 5.26 (s, 2 H), 2.49 (d, J=2.78 Hz, 3 H).

Workup

  1. washwashed with water
  2. concentrationThe organic layer is concentrated
  3. customthe residue is separated with FCC (EtOAc/heptane from 0 to 20%)

Sources & evidence

ORD record
ord-8cc08a9dd6aa4672b55aa34bc3375e5d
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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