Diisopropylethylamine → HCID 10487441, compound

HRID 2069120Notes

Reaction equation

HRID 2069120 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].CCN(C(C)C)C(C)C.[CH2:19](Br)[O:20][CH3:21]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:19][O:20][CH3:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83093Bromomethyl methyl etherHCID 1230512,4-Difluorophenol

Product 1

HCID 10487441HCID 10487441, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-difluorophenol (11.0 g, 85 mmol) and DIPEA (15.5 mL, 89 mmol) in DCM (150 ml) at 0° C. under nitrogen was added MOM-Br (7.33 mL, 89 mmol) over 1 hr and the reaction mixture then maintained at RT for 16 hr. The resulting mixture was washed successively with water, aq 2M NaOH solution, water and brine, and was then dried (MgSO4) and evaporated in vacuo to afford 2,4-difluoro-1-(methoxymethoxy)benzene as a colourless oil (13.7 g, 88% yield). Rt 3.17 min (Method 1, basic, no ionization observed), which was used directly in the next step (below).

Workup

  1. washThe resulting mixture was washed successively with water, aq 2M NaOH solution, water and brine
  2. dry with materialwas then dried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-a86b2bf9d7a14dafac6b68145776246c
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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