2-Chloro-6-methylphenol → HCID 67246220, compound

HRID 1695259Notes

Reaction equation

HRID 1695259 reaction equation
C(N(CC)CC)C.Br[CH2:9][C:10]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:11]=1[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].ClC1C=CC=C(C)C=1O.C([SiH](C)C)(C)(C)C.BrN1C(=O)CCC1=O.[CH3:49][O:50][C:51](=[O:61])[C:52]1[CH:57]=[C:56]([CH3:58])[C:55]([Br:59])=[C:54]([SH:60])[CH:53]=1>C(Cl)(Cl)Cl.CO>[CH3:49][O:50][C:51](=[O:61])[C:52]1[CH:57]=[C:56]([CH3:58])[C:55]([Br:59])=[C:54]([S:60][CH2:9][C:10]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:11]=2[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:53]=1

Participants

9

Reactant 6

HCID 68982-Chloro-6-methylphenolHCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 5072427tert-ButyldimethylsilaneHCID 57999891HCID 57999891, compoundHCID 67246834HCID 67246834, compound

Product 1

HCID 67246220HCID 67246220, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

Triethyl amine (36 mL, 0.263 mol) was added to a solution of (2-bromomethyl-6-chloro-phenoxy)-tert-butyl-dimethyl-silane (72 g, 0.214 mol) [prepared from 6-chloro cresol by protecting the hydroxy group with t-butyldimethylsilane followed by bromination using N-bromosuccinimide] and compound of Example 1f (43 g, 0.164 mol) in chloroform (600 mL) at 5° C. over a period of 20 min. The reaction mixture was stirred at 25° C. for 30 min. The reaction mixture was washed with water (2×200 mL) and brine (100 mL). The solvent was removed under reduced pressure and to the oily mass obtained, methanol (300 mL) was added with stirring. The crystalline solid obtained was filtered, washed with methanol and dried to obtain the title compound. Yield: 70 g, (83%); 1H NMR (CDCl3, 300 MHz): δ 0.28 (s, 6H, 2CH3), 1.03 (s, 9H, 3CH3), 2.45 (s, 3H, CH3), 3.89 (s, 3H, OCH3), 4.19 (s, 2H, CH2), 6.89 (t, 1H, Ar), 7.24 (t, 1H, Ar), 7.32 (d, 1H, Ar), 7.61 (s, 1H, Ar), 7.69 (s, 1H, Ar); MS: m/e (ES−) 515 (M−1).

Workup

  1. customat 5° C.
  2. customof 20 min
  3. washThe reaction mixture was washed with water (2×200 mL) and brine (100 mL)
  4. customThe solvent was removed under reduced pressure and to the oily mass
  5. customobtained
  6. stirringwith stirring
  7. customThe crystalline solid obtained
  8. filtrationwas filtered
  9. washwashed with methanol
  10. customdried

Sources & evidence

ORD record
ord-7165219f102648d2b5621f1737dc1d82
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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