Water → HCID 86685093, compound

HRID 1750853Notes

Reaction equation

HRID 1750853 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10]([OH:13])([CH3:12])[CH3:11].Cl[CH2:15][O:16][CH2:17][CH3:18].O>CN(C=O)C.CCN(C(C)C)C(C)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10]([O:13][CH2:15][O:16][CH2:17][CH3:18])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 86685094Benzenemethanol, 2-bromo-4-fluoro-α,α,5-trimethyl-

Product 1

HCID 86685093HCID 86685093, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21988380HCID 21988380, compoundSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(2-bromo-4-fluoro-5-methylphenyl)propan-2-ol (2.0 g, 8.1 mmol) in DMF:DIPEA (2:1, 9 mL) was added (chloromethoxy)ethane (1.53 g, 16.2 mmol). The reaction mixture was heated at 100° C. in microwave equipment for 1.5 h. Water (200 mL) was added and the mixture was extracted with DCM (200 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (30:1) to give 1-bromo-2-(2-(ethoxymethoxy)propan-2-yl)-5-fluoro-4-methylbenzene (2.2 g, 89%) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.208-7.234 (m, 2H), 4.572 (s, 2H), 3.594 (q, J=7.0 Hz, 2H), 2.149 (s, 3H), 1.665 (s, 6H), 1.115 (t, J=7.0 Hz, 3H) ppm.

Workup

  1. extractionthe mixture was extracted with DCM (200 mL×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with PE-EA (30:1)

Sources & evidence

ORD record
ord-a1dfd8723e5541a4a6796699ac15e596
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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