Carbon tetrabromide → HCID 14180975, compound

HRID 1722426Notes

Reaction equation

HRID 1722426 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][CH2:33][NH:34][C:35](=[O:45])[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[CH:30]=2)[NH:25][CH:24]=1.C(Br)(Br)(Br)[Br:47]>C(Cl)Cl>[Br:47][CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][CH2:33][NH:34][C:35](=[O:45])[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[CH:30]=2)[NH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14180974HCID 14180974, compound

Product 1

HCID 14180975HCID 14180975, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (149 mg) in dry CH2Cl2 (0.5 ml) was added dropwise at -10° to -5° under nitrogen to a stirred solution of the compound of section (a) (155 mg) and CBr4 (139 mg) in dry CH2Cl2 (10 ml). After stirring at room temperature for 20 h (overnight) the solution was evaporated in the presence of silica gel and the resultant fine powder was chromatographed [elution with EA:hexane (1:1)] to give the title compound as a pale yellow viscous oil (117 mg). T.l.c. EA, Rf 0.51 (major).

Workup

  1. customwas evaporated in the presence of silica gel
  2. customthe resultant fine powder was chromatographed
  3. wash[elution with EA:hexane (1:1)]

Sources & evidence

ORD record
ord-b34dc6f83d6d4ab28213f354f7a2efe6
Source dataset
uspto-grants-1989_08
Patent number
US04855314

Reaction notes

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