Trityl chloride → HCID 9855190, compound

HRID 991163Notes

Reaction equation

HRID 991163 reaction equation
[C-:1]#[N:2].[F:3][C:4]1[C:9]([B:10]([C:22]2[C:27]([F:28])=[C:26]([F:29])[C:25]([F:30])=[C:24]([F:31])[C:23]=2[F:32])[C:11]2[C:16]([F:17])=[C:15]([F:18])[C:14]([F:19])=[C:13]([F:20])[C:12]=2[F:21])=[C:8]([F:33])[C:7]([F:34])=[C:6]([F:35])[C:5]=1[F:36].[F:37][C:38]1[C:43]([B:44]([C:56]2[C:61]([F:62])=[C:60]([F:63])[C:59]([F:64])=[C:58]([F:65])[C:57]=2[F:66])[C:45]2[C:50]([F:51])=[C:49]([F:52])[C:48]([F:53])=[C:47]([F:54])[C:46]=2[F:55])=[C:42]([F:67])[C:41]([F:68])=[C:40]([F:69])[C:39]=1[F:70].[K+].Cl[C:73]([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)([C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1>ClCCl>[C-:1]#[N:2].[F:28][C:27]1[C:22]([B:10]([C:9]2[C:4]([F:3])=[C:5]([F:36])[C:6]([F:35])=[C:7]([F:34])[C:8]=2[F:33])[C:11]2[C:12]([F:21])=[C:13]([F:20])[C:14]([F:19])=[C:15]([F:18])[C:16]=2[F:17])=[C:23]([F:32])[C:24]([F:31])=[C:25]([F:30])[C:26]=1[F:29].[F:62][C:61]1[C:56]([B:44]([C:43]2[C:38]([F:37])=[C:39]([F:70])[C:40]([F:69])=[C:41]([F:68])[C:42]=2[F:67])[C:45]2[C:46]([F:55])=[C:47]([F:54])[C:48]([F:53])=[C:49]([F:52])[C:50]=2[F:51])=[C:57]([F:66])[C:58]([F:65])=[C:59]([F:64])[C:60]=1[F:63].[C:74]1([C+:73]([C:80]2[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=2)[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][CH:91]=2)[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 86758097HCID 86758097, compound

Product 1

HCID 9855190HCID 9855190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Potassium bis(tris(pentafluorophenyl)borane)cyanide (827.5 mg, 0.7598 mmol) and chlorotriphenylmethane (211.8 mg, 0.7597 mmol) were placed in a 50 mL flask. The stirred solids were taken up in 10 mL of dichloromethane, added via syringe under argon counter-flow. An immediate reaction gave a deep yellow solution and a colorless solid. The solid was removed by filtration and washed (four times 4 mL) until all color was gone. The filtrate was reduced under vacuum to 4 mL, cooled to −78° C. and diluted with 10 mL of hexanes. The resulting suspension of brown oil was allowed to warm and stir. The oil solidified and then digested to a canary-yellow solid after stirring for 30 minutes. The yellow solid was isolated by filtration and dried under high vacuum. Yield, 935.3 mg, 95.20 percent.

Workup

  1. additionadded via syringe under argon counter-flow
  2. customAn immediate reaction
  3. customgave a deep yellow solution
  4. customThe solid was removed by filtration
  5. washwashed (four times 4 mL) until all color
  6. additiondiluted with 10 mL of hexanes
  7. additionThe resulting suspension of brown oil
  8. temperatureto warm
  9. stirringafter stirring for 30 minutes
  10. customThe yellow solid was isolated by filtration
  11. customdried under high vacuum
  12. customYield

Sources & evidence

ORD record
ord-154e29dbd58c4aeb9a4604f37caabb42
Source dataset
uspto-grants-2002_10
Patent number
US06462156B2

Reaction notes

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