Dichloromethane → HCID 67392140, compound

HRID 1916997Notes

Reaction equation

HRID 1916997 reaction equation
C[C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=[CH:4][C:3]=1[O:21]C.B(Br)(Br)Br.[CH2:27](Cl)Cl>>[CH2:9]([NH:8][C:7]1[CH:2]=[C:3]([OH:21])[CH:4]=[CH:5][C:6]=1[CH3:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 67391782HCID 67391782, compound

Product 1

HCID 67392140HCID 67392140, compoundYield 70%

Conditions

Temperature
0 °C

Procedure

As a general methyl group de-protection procedure, 4 methyl-3-dodecylamino-1-methoxy benzene 120 was suspended in dry CH2Cl2, cooled to 0° C. and 5 equivalents of a solution of BBr3 (1M CH2Cl2, Aldrich Chem. Co.) were added and the reaction maintained at 0° C. for 16 hours. The reaction was quenched at 0° C. by slow addition of MeOH and then careful addition of solid NaHCO3 (10 Equiv.) until foaming stops. The mixture was filtered, the filtrate was concentrated to an oil, and the product was isolated by normal phase chromatography eluting with methanol/CH2Cl2. The solvent was removed from the pure fractions to give 3-dodecylamino-1-hydroxy-4 methylbenzene 120 (R═H, R′═R′″═H, R″=Me) as a waxy solid in 70-80% yield (1HNMR (CDCl3) δ 6.91 (d, 1H), 6.17 (d, 1H), 6.14 (dd, 1H) 4.62 (bs, OH), 3.53 (bs, NH), 3.14 (t, 2 H), 2.09 (s, 3 H), 1.70 (p, 2 H), 1.46 (m, 18H), 0.93 (t, 3H))

Workup

  1. temperaturethe reaction maintained at 0° C. for 16 hours
  2. customThe reaction was quenched at 0° C. by slow addition of MeOH
  3. additioncareful addition of solid NaHCO3 (10 Equiv.)
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated to an oil
  6. customthe product was isolated by normal phase chromatography
  7. washeluting with methanol/CH2Cl2
  8. customThe solvent was removed from the pure fractions

Sources & evidence

ORD record
ord-0e542f4987e04b709c9706f86fb52746
Source dataset
uspto-grants-2013_12
Patent number
US08618161B2

Reaction notes

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