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Product Details of 2-Bromo-4-methylphenol

CAS No. :6627-55-0
Formula : C7H7BrO
M.W : 187.03
SMILES Code : OC1=CC=C(C)C=C1Br
MDL No. :MFCD00002151
InChI Key :MTIDYGLTAOZOGU-UHFFFAOYSA-N
Pubchem ID :23109

Safety of 2-Bromo-4-methylphenol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Bromo-4-methylphenol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 6627-55-0 ]
  • Downstream synthetic route of [ 6627-55-0 ]

[ 6627-55-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 6627-55-0 ]
  • [ 107-30-2 ]
  • [ 104750-60-9 ]
YieldReaction ConditionsOperation in experiment
86% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 18 h; In a typical procedure, the appropriate bromophenol (11 mmol, 1.0 eq) was taken up in dry THF (20 mL) under N2 and cooled to 0 °C. DIEA (2.8 mL, 16 mmol, 1.5 eq) was added followed by dropwise addition of MOMCI (1.2 mL, 16 mmol, 1.5 eq). The reaction was allowed to stir and warm to RT over 18 h. The THF was removed and the crude material was redissolved in EtOAc and washed with 2 M NaOH and water. The organic layer was dried over Na2S04 and the crude material was purified by flash chromatography.
Synthesized by General Method A. Purified by flash chromatography (Biotage FLASH 40M KP-Sil silica, 4percent Et20/hexane) to yield 2.12 g (86percent) of 22 as clear viscous oil. 1H NMR (CD2C12, 300 MHz) : 7.36 (d, J=1.4 Hz, 1H), 7.10-6.97 (m, 2H), 5.18 (s, 2H), 3.49 (s, 3H), 2.27 (s, 3H).
References: [1] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 12, p. 1994 - 2004.
[2] Chemistry - A European Journal, 2007, vol. 13, # 22, p. 6365 - 6378.
[3] Patent: WO2005/108406, 2005, A1, . Location in patent: Page/Page column 103-104; 121-122.
[4] Organic Letters, 2015, vol. 17, # 20, p. 5036 - 5039.
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6703 - 6707.
  • 2
  • [ 109-87-5 ]
  • [ 6627-55-0 ]
  • [ 104750-60-9 ]
YieldReaction ConditionsOperation in experiment
92% With toluene-4-sulfonic acid In dichloromethane for 72 h; Inert atmosphere; Molecular sieve; Reflux 4a. Prepara ion of 2-bromo-l-(methoxymethoxy)-4-methylbenzene.
2-Bromo-4-methylphenol (13.1 g, 70.0 mmol), dimethoxymethane (35 mL), p-toluene- sulfonic acid (100 mg) and methylene chloride (300 mL) were heated, under reflux, in a nitrogen atmosphere for three days, using a Soxhlet condenser containing activated 3A molecular sieves. The molecular sieves were exchanged for newly activated ones after every 24 hours. The reaction mixture was cooled, and the volatiles were removed by rotary evaporation. The residue was taken up in 100 mL of ether, and washed successively with 100 mL of 2M sodium hydroxide solution, 100 mL of water and 100 mL of brine. The organic layer was dried over anhydrous magnesium sulfate and passed through a small bed of silica gel. Removal of the solvent gave 14.5 g (92percent) of pure 2, as a pale yellow oil, which was used as such for the next step. 1H NMR (CDC13) δ 7.40 (m, 1H), 7.07 (m, 2H), 5.25 (s, 2H), 3.55 (s, 3H) and 2.31 (s, 3H).
References: [1] Patent: WO2016/3878, 2016, A1, . Location in patent: Page/Page column 51.
  • 3
  • [ 13057-17-5 ]
  • [ 6627-55-0 ]
  • [ 104750-60-9 ]
References: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 20, p. 4005 - 4011.
  • 4
  • [ 6627-55-0 ]
  • [ 144-55-8 ]
  • [ 107-30-2 ]
  • [ 7087-68-5 ]
  • [ 104750-60-9 ]
References: [1] Patent: US2019/77784, 2019, A1, .
 

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