Water → HCID 86685505, compound

HRID 1037062Notes

Reaction equation

HRID 1037062 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Cl:9])=[CH:4][C:3]=1[C:10]([OH:13])([CH3:12])[CH3:11].Cl[CH2:15][O:16][CH2:17][CH3:18].CCN(C(C)C)C(C)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Cl:9])=[CH:4][C:3]=1[C:10]([O:13][CH2:15][O:16][CH2:17][CH3:18])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 86685506HCID 86685506, compound

Product 1

HCID 86685505HCID 86685505, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(2-bromo-5-chloro-4-methylphenyl)propan-2-ol (4.5 g 17.1 mmol), (chloromethoxy)ethane (3.2 g, 34.2 mmol) and DIPEA (6.6 g, 51.3 mmol) in DCM (50 mL) was stirred at 40° C. overnight under argon. Water (50 mL) was added and the mixture was extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with PE-EA (10:1) to give 1-bromo-4-chloro-2-(2-(ethoxymethoxy)propan-2-yl)-5-methylbenzene (4.27 g, yield 77.5%). 1H NMR (400 MHz, DMSO-d6): δ 7.67 (s, 1H), 7.50 (s, 1H), 4.59 (s, 2H), 3.55 (q, 2H), 2.29 (s, 3H), 1.65 (s, 6H), 1.08 (t, 3H) ppm; MS: m/z=344.8 (M+Na+, ESI+).

Workup

  1. extractionthe mixture was extracted with DCM (2×50 mL)
  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 silica gel column chromatography
  7. washeluted with PE-EA (10:1)

Sources & evidence

ORD record
ord-d0c7a76e264242aebcf97c1e5a7dbe39
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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