Tetrafluoroboric acid → Tricyclohexylphosphonium tetraphenylborate

HRID 13866

Reaction equation

[CH:1]1([P:7]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.[H+].F[B-](F)(F)F.C1([PH+](C2CCCCC2)C2CCCCC2)CCCCC1.[C:50]1([B-:56]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.[Na+]>>[C:69]1([B-:56]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1.[CH:14]1([PH+:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

Reactant 4

HCID 28118Tetrafluoroboric acid

HCID 75806Tricyclohexylphosphine

HCID 2723787Sodium Tetraphenylborate

HCID 11710396Tricyclohexylphosphonium Tetrafluoroborate

Product 1

HCID 23136635Tricyclohexylphosphonium tetraphenylborateYield 75%

Procedure

Tricyclohexylphosphine is reacted with fluoroboric acid to synthesize tricyclohexylphosphonium tetrafluoroborate, which is reacted with sodium tetraphenylborate to produce tricyclohexylphosphonium tetraphenylborate (75% yield). A similar process is described in which tri-tert-butylphosphine is used as starting material to produce tri-tert-butylphosphonium tetraphenylborate (71% yield) (see Nonpatent Document 4).

Sources & evidence

ORD record: ord-26bcb57d0e5a476a8aaa17b3207a4354
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728176B2

Linked notes

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